DE2250377A1 - 4,6-Disubst. resorcinol derivs - with e.g. psychopharmacological activity - Google Patents
4,6-Disubst. resorcinol derivs - with e.g. psychopharmacological activityInfo
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- DE2250377A1 DE2250377A1 DE19722250377 DE2250377A DE2250377A1 DE 2250377 A1 DE2250377 A1 DE 2250377A1 DE 19722250377 DE19722250377 DE 19722250377 DE 2250377 A DE2250377 A DE 2250377A DE 2250377 A1 DE2250377 A1 DE 2250377A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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Abstract
Description
4,6-disubstituierte Resorcinverbindungen Gegenstand der Erfindung sind neue 4,6-disubstituierte Resorcinverbindungen der allgemeinen Formel worin bedeuten A) R¹, R²,R5 und R6 = H oder Niedrigalkyl und R4 = H, 3 7 wenn R3 und R7 einen Rest N(R8)2, R8 = H, Niedrigalkyl R9 t H, Niedrigalkyl, Phenyl, subst. Phenyl, 10: geradkettiges oder verzweigtes Niedrig alkylen, R11= H, Niedrigalkyl, CH2-CH2-N t 8 ) 2 ' CH2-CH2-OR oder B) R² zusammen mit R³ und R6 zusammen mit R7 jeweils einen 3-Piperazin-2-on-Ring bilden können, wenn R4 = H ist; C) R7 einen Dialkylamino-, N-Piperidino-, N-Morpholino-oder N-Piperazinorest, der in N'-Stellung durch Niedrig alkyl oder Aminoalkyl substituiert ist, bedeuten kann, wenn R3 und -4 unter Ausbildung eines #-Pyranringes verbunden sind; D) R6 und R7 zusammen einen 3,4-Dihydro-2-chinoxalinonrest oder 3,4-Dihydro-1,4-benzoxazin-2-onrest darstellen, wenn R2 einen Carboxyäthylrest und R3 und R4 eine Bindung unter Ausbildung eines t-Pyranringes bedeuten.4,6-disubstituted resorcinol compounds The invention relates to new 4,6-disubstituted resorcinol compounds of the general formula in which A) R¹, R², R5 and R6 = H or lower alkyl and R4 = H, 3 7 when R3 and R7 are a radical N (R8) 2, R8 = H, lower alkyl R9 t H, lower alkyl, phenyl, subst. Phenyl, 10: straight-chain or branched lower alkylene, R11 = H, lower alkyl, CH2-CH2-N t 8) 2 'CH2-CH2-OR or B) R² together with R³ and R6 together with R7 are each a 3-piperazine-2 -on ring when R4 = H; C) R7 is a dialkylamino, N-piperidino, N-morpholino or N-piperazino radical which is substituted in the N'-position by lower alkyl or aminoalkyl, if R3 and -4 are connected to form a # -pyran ring are; D) R6 and R7 together represent a 3,4-dihydro-2-quinoxalinone radical or 3,4-dihydro-1,4-benzoxazin-2-one radical when R2 is a carboxyethyl radical and R3 and R4 are a bond with the formation of a t-pyran ring mean.
Niedrigalkyl und Niedrigalkylen bedeutet, dass diese Reste 1 bis 6, vorzugsweise 1 bis LI C-Atome enthalten Die neuen Verbindungen sind wertvolle pharmakologische Produkte mit psychopharmakologischen, antiphlogistischen, chemotherapeutischen, immunosuppressiven-Eigenschaften sowie Herz- und Kreislauf-Wirkung. Sie sind auch als Zwischenprodukte zur Herstellung wertvoller pharmakologischer Produkte geeignet.Lower alkyl and lower alkylene means that these radicals 1 to 6, preferably contain 1 to LI carbon atoms. The new compounds are valuable pharmacological Products with psychopharmacological, anti-inflammatory, chemotherapeutic, immunosuppressive properties as well as cardiovascular effects. You are too suitable as intermediate products for the production of valuable pharmacological products.
Die neuen Verbindungen können nach den folgenden Reaktionsschemen hergestellt werden: Die substituierten Acetophenon-Derivate II können mit Amidacetalen zu III bzw. durch Esterkondensation zu IV umgesetzt werden; III und IV lassen sich entweder direkt oder nach Umwandlung in V durch Reaktion mit Aminen- zu T umsetzen.The new compounds can be made according to the following reaction schemes: The substituted acetophenone derivatives II can be reacted with amide acetals to III or by ester condensation to IV; III and IV can be converted to T either directly or after conversion to V by reaction with amines.
Beispiele 4,6-Di(#-dimethylaminomethylen)-acetyl-resorein 26,2 g 4 4,6-Diacetylresorcin werden mit 16,1 g Dimethylformamiddiäthylacetal in 100 ml sied. Xylol 2 Stunden rückfliessend erhitzt, wobei das entstehende Methanol abdestilliert wird. Nach dem Erkalten saugt man den Niederschlag ab und kristallisiert aus Dimethylformamid um. Examples 4,6-di (# - dimethylaminomethylene) acetyl resorein 26.2 g 4 4,6-diacetylresorcinol are mixed with 16.1 g of dimethylformamide diethyl acetal in 100 ml simmer. Xylene heated to reflux for 2 hours, the methanol formed being distilled off will. After cooling, the precipitate is filtered off with suction and crystallized from dimethylformamide around.
Ausbeute 85 % d.Th. Gelbe Kristalle, Schmp. 2800 (DMFA).Yield 85% of theory Yellow crystals, m.p. 2800 (DMFA).
UVmax.: 373, 339, 267 nm (Dioxan) Analyse: Ber.: Ç 63,14 H 6,62 N 9,20 Gef.: C 62,86 H 6,20 N 9,26 4,6-Di(#-piperidinemethylen)-acetyl-resorein 21,42 g Benzo(1,2-b:5,4-b')-bi-4-pyron werden in 500 ml siedendem äthanol gelöst und mit 18,73 g Piperidin 2 Stunden am Rückfluss gekocht. Man lässt die Lösung erkalten und saugt, evtl. nach Einengung, die ausgefallenen Kristalle ab.UVmax .: 373, 339, 267 nm (dioxane) Analysis: Calc .: Ç 63.14 H 6.62 N 9.20 Found: C 62.86 H 6.20 N 9.26 4,6-Di (# - piperidinemethylene) -acetyl-resorein 21.42 g of benzo (1,2-b: 5,4-b ') - bi-4-pyrone are dissolved in 500 ml of boiling ethanol and refluxed with 18.73 g of piperidine for 2 hours. The solution is allowed to cool and sucks off the precipitated crystals, possibly after concentration.
Ausbeute: 95 % d.Th.Yield: 95% of theory
gelbe Nadeln, F = 298° C (Dimethylformamid) UVmax: 375, 341, 267 nm (Dioxan) Analyse: Ber.: 68,73 % C Gef.: 69,14 g C 7,34 % H 7,08 % H 7,28 % N 7,37 % N 4,6-Di(#-morpholinomethylen)-acethyl-resorein 2 g Benzo(1,2-b:5,4-b')-bi-pyron werden in ca. 60 ml Morpholin 1 Stunde am RUckfluss gekocht. Nach Abkühlung werden die ausgefallenen Kristalle abgesaugt.yellow needles, F = 298 ° C (dimethylformamide) UVmax: 375, 341, 267 nm (Dioxane) Analysis: Calc .: 68.73% C Found: 69.14 g C 7.34% H 7.08% H 7.28% N 7.37 % N 4,6-di (# - morpholinomethylene) -acethyl-resorein 2 g benzo (1,2-b: 5,4-b ') - bi-pyrone are refluxed in about 60 ml of morpholine for 1 hour. After cooling down the precipitated crystals sucked off.
Ausbeute: 95 % d.Th.Yield: 95% of theory
gelbe Nadeln, F = 2900C (Dimethylformamid) UVmax: 373, 340, 268 nm (Dioxan) Analyse: Ber.: 61,85 % C Gef.: 62,04 % C 6,23 % H 6,15 % H 7,21 % N 7,14 % N 6-(#-Morpholinomethylen)-acetyl-7-hydroxy-chromon 21,42 Benzo(1,2-b:5,4-b')-bi-4-pyron werden in 500 ml siedendem Alkohol gelöst und mit 19,1 g Morpholin 2 Stunden am Rückfluss gekocht. Nach Abkühlung werden die ausgefallenen Kristalle abgesaugt.yellow needles, F = 2900C (dimethylformamide) UVmax: 373, 340, 268 nm (Dioxane) Analysis: Calc .: 61.85% C Found: 62.04% C 6.23% H 6.15 % H 7.21% N 7.14% N 6 - (# - morpholinomethylene) -acetyl-7-hydroxy-chromone 21.42 benzo (1,2-b: 5,4-b ') - bi-4- pyron are dissolved in 500 ml of boiling alcohol and treated with 19.1 g of morpholine for 2 hours Boiled under reflux. After cooling, the precipitated crystals are filtered off with suction.
Ausbeute: 90 % d.Th.Yield: 90% of theory
gelbe Kristalle, F = 2730 C (Dimethylformamid), MG (MS): M 301 UVmax: 369, 256 nm (Dioxan) Analyse: Ber.: 63,78 % C Gef.: 63,62 % C 5,02 % H 5,13 % H 4,64 % N 4,65 % N 26,54 % 0 26y92 % 0 4,6-Di(Z-hydroxyäthylaminomethylen)-acetyl-resorcin 21,42 g Benzo(1,2-b:5,4-b')-bi-4-pyron werden'In 500 ml siedendem Alkohol gelöst und mit 13,44 g Aminoäthanol 2 Stunden am Rückfluss gekocht. Nach Abkühlung werden die ausgefallenen Kristall abgesaugt.yellow crystals, F = 2730 C (dimethylformamide), MG (MS): M 301 UVmax: 369, 256 nm (dioxane) Analysis: Calc .: 63.78% C Found: 63.62% C, 5.02% H, 5.13% H 4.64% N 4.65% N 26.54% 0 26y92% 0 4,6-di (Z-hydroxyethylaminomethylene) acetyl resorcinol 21.42 g of benzo (1,2-b: 5,4-b ') - bi-4-pyrone become' in 500 ml boiling Dissolved alcohol and refluxed with 13.44 g of aminoethanol for 2 hours. To After cooling, the precipitated crystals are sucked off.
Ausbeute: 70 % d. Th.Yield: 70% of theory Th.
gelbe Kristalle, F = 1870 C (Isopropanol) UVmax: 378, 343, 266 nm (Dioxan) Analyse: Ber.: 57,14 % C Gef.: 57,22 % C 5,99 % H 5,81 % H 8,33 % N 7,99 % N 4,6-Di(#-aminoäthylaminomethylen)-acetyl-resorein 21,42 g Benzo(1,2-b:5,4-b')-bi-4-pyton werden in 500 ml siedendem Alkohol gelöst und mit 13,22 g Athylendiamin 2 Stunden am Rückfluss gekocht. Nach Abkühlung werden die ausgefallenen Kristalle abgesaugt.yellow crystals, m.p. 1870 C (isopropanol) UVmax: 378, 343, 266 nm (Dioxane) Analysis: Calc .: 57.14% C Found: 57.22% C 5.99% H 5.81% H 8.33% N 7.99 % N 4,6-di (# - aminoethylaminomethylene) -acetyl-resorein 21.42 g benzo (1,2-b: 5,4-b ') - bi-4-pyton are dissolved in 500 ml of boiling alcohol and treated with 13.22 g of ethylenediamine for 2 hours boiled on reflux. After cooling, the precipitated crystals are filtered off with suction.
Ausbeute: 40 % d. Th.Yield: 40% of theory Th.
gelbe Kristalle, F = 300° C (Zersetzung) UVmax: 321, 257 nm (Essigsäure) Analyse: Ber.: 57,47 % C Gef.: 57,93 % C 6,63 % H 6,og % H 16,76 % N 16,00 % N 4,6-Di(-dimethylaminoRthylaminomethylen)-acetyl-resorcin 21,42 g Benzo(1,2-b:5,4-b')-bi-4-pyron werden in 500 ml siedendem Alkohol gelöst und mit 16,08 g N,N-Dimethyläthylendiamin 2 Stunden am Rückfluss gekocht. Nach Abkühlung werden die ausgefallenen Kristalle abgesaugt.yellow crystals, F = 300 ° C (decomposition) UVmax: 321, 257 nm (acetic acid) Analysis: Calc .: 57.47% C Found: 57.93% C 6.63% H 6, og% H 16.76% N 16.00% N 4,6-Di (-dimethylaminoRthylaminomethylene) -acetyl-resorcinol 21.42 g of benzo (1,2-b: 5,4-b ') - bi-4-pyrone are dissolved in 500 ml of boiling alcohol and refluxed with 16.08 g of N, N-dimethylethylenediamine for 2 hours. After cooling down the precipitated crystals are filtered off with suction.
Ausbeute: 55 % d.Th.Yield: 55% of theory
gelbe Kristalle, F = 820 C (Äthanol) UVmax: 371, 336, 266 nm (Dioxan) Analyse: Ber.: 61,52 % C Gef.: 59,95 % C 7,74 f H 7,24 % H 14,35 % N 14,05 % N Nach dem folgenden Formelschema: kann aus VI die Verbindung 2,8-DicarbSthoxy-benzo-(1,2-b:5,4-b')-bi-4-pyron (VII) gewonnen werden und daraus sind weitere der neuen Verbindungen darstellbar.yellow crystals, F = 820 C (ethanol) UVmax: 371, 336, 266 nm (dioxane) Analysis: Calc .: 61.52% C Found: 59.95% C 7.74 f H 7.24% H 14 , 35% N 14.05% N According to the following equation: the compound 2,8-dicarb-thoxy-benzo- (1,2-b: 5,4-b ') -bi-4-pyrone (VII) can be obtained from VI and further of the new compounds can be prepared therefrom.
Stufe A: 2-Carbäthoxy-6-acetyl-7-oxy-chromon In einem Dreihalskolben mit Rührer und Rückflusskühler werden 6,9 g Natrium in 100 ml absolutem Alkohol gelöst.Stage A: 2-carbethoxy-6-acetyl-7-oxy-chromone in a three-necked flask using a stirrer and reflux condenser, 6.9 g of sodium are dissolved in 100 ml of absolute alcohol solved.
Dazu gibt man eine Lösung von 9,7 g Diacetalresorcin und 16,2 g Oxalsäurediäthylester in 150 ml siedendem Alkohol.A solution of 9.7 g of diacetal resorcinol and 16.2 g of diethyl oxalate is added in 150 ml of boiling alcohol.
Nach einstündigem Rühren in der Siedehitze saugt man ab, hydrolysiert mit 100 ml 3 n Schwefelsäure durch zweistündiges Erhitzen.After stirring for one hour at the boiling point, the mixture is filtered off with suction and hydrolyzed with 100 ml of 3N sulfuric acid by heating for two hours.
Ausbeute: 70 % d.Th.Yield: 70% of theory
farblose Kristalle, F = 1580 C (Äthanol) Analyse: Ber.: 60,87 % C Gef.: 59,96 % C 4,38 % H 4,45 % H Stufe 13: 2,8-Dicarbäthoxy-benzo(1,2-b:5,4-b' )-bi-4-pyron In einem Dreihalskolben mit Rührer und Rückflusskühler werden 6,9 g Natrium in 100 ml absolutem Alkohol gelöst. colorless crystals, F = 1580 C (ethanol) Analysis: Calc .: 60.87% C Found: 59.96% C 4.38% H 4.45% H Level 13: 2,8-dicarbethoxy-benzo (1,2-b: 5,4-b ' ) -bi-4-pyrone In a three-necked flask with stirrer and reflux condenser are 6.9 g Sodium dissolved in 100 ml of absolute alcohol.
x und cyclisiert dann in Alkohol mit Schwefelsäure Dann gibt man eine Lösung von 27,6 g 2-Carbäthoxy-6-acetyl-7-oxy-chromon und 8,1 g Oxalsäurediäthylester in 150 ml siedendem Alkohol. Nach einstündigem Rühren in der Siedehitze saugt man ab, hydrolysiert mit 100 ml 3 n Schwefelsäure und cyclisiert dann in Alkohol mit Schwefelsäure durch zweistündiges Erhitzen.x and then cyclizes in alcohol with sulfuric acid then a solution of 27.6 g of 2-carbethoxy-6-acetyl-7-oxychromone and 8.1 g of diethyl oxalate is added in 150 ml of boiling alcohol. After stirring for one hour at the boiling point, suction is carried out from, hydrolyzed with 100 ml of 3N sulfuric acid and then cyclized in alcohol with Sulfuric acid by heating for two hours.
Ausbeute: 50 % d.Th.Yield: 50% of theory
farblose Kristalle, F = 233° C (Äthanol) Analyse: Ber.: 60,34 % C Gef.: 59,37 % C 3,94 % H 4,13 % H 4,6-Dihydroxy-isophthaloyldimethylen-di-(3-piperazin-2-on) 35,8 g 2,8-Dicarbäthoxy-benzo(1,2-b:5,4-b')-bi-4-pyron werden in 150 ml siedendem Alkohol gelöst und. mit 13, 22 g Äthylendiamin 2 Stunden am Rückfluss erhitzt. Nach Erkalten der Lösung saugt man, wenn nötig nach Einengung, die ausgefallenen Kristalle ab.colorless crystals, F = 233 ° C (ethanol) Analysis: Calc .: 60.34% C Found: 59.37% C 3.94% H 4.13% H 4,6-dihydroxy-isophthaloyldimethylene-di- (3-piperazin-2-one) 35.8 g of 2,8-dicarbethoxy-benzo (1,2-b: 5,4-b ') - bi-4-pyrone are boiled in 150 ml Alcohol dissolved and. heated under reflux for 2 hours with 13, 22 g of ethylenediamine. To When the solution cools, the crystals which have precipitated out are sucked off, if necessary after concentration away.
Ausbeute: 75 % d.Th.Yield: 75% of theory
gelbe Kristalle, F = ca. 3000 C (Zersetzung) UVmax: 40,1 370, 267 nm (Dioxan) Analyse: Ber.: 56,55 % C Gef.: 56,26 % C 3,69 %H 4,70 % H 14,65 % N 14,06 % N 3-[6(2-Carbonsäureäthylester-7-hydroxyl-chromonyl)-acetyliden]-3,4-dihydro-2(1H)-chiunoxalon 35,8 g 2,8-Dicathoxy-benzo(1,2-b;5,4-b')-bi-4-pyron werden in 150 ml siedendem Alkohol gelöst und mit 23,8 g o-Phenylendiamin 2 Stunden am RUckfluss erhitzt.yellow crystals, F = approx. 3000 C (decomposition) UVmax: 40.1 370, 267 nm (dioxane) Analysis: Calc .: 56.55% C Found: 56.26% C 3.69% H 4.70% H 14.65% N 14.06% N 3- [6 (2-Carboxylic acid ethyl ester-7-hydroxyl-chromonyl) -acetylidene] -3,4-dihydro-2 (1H) -chiunoxalone 35.8 g of 2,8-dicathoxy-benzo (1,2-b; 5,4-b ') -bi-4-pyrone are dissolved in 150 ml of boiling alcohol dissolved and refluxed with 23.8 g of o-phenylenediamine for 2 hours.
Nach Erkalten der Lösung saugt man, wenn nötig nach Einengung, die ausgefallenen Kristalle ab.After the solution has cooled down, the precipitated crystals.
Ausbeuto: 50 % d.Th.Yield: 50% of theory
orangefarbene Nadeln, F = 3560 C (DMFA) UVmax: 461, 437, 276, 225 nm (Dioxan) Analyse: Ber.: 62,86 % C Gef.: 62,83 S C 3,84 S H 3,96 % H 6,66 % N 6,63 % N 3-[6-(2-Carbonsäureäthylester-7-hydroxy-chromonyl)-acetyliden]-3,4-dihydro-2H-1,4-benzoxazin-2-on 35,8 g 2,8-Dicarbäthoxy-benzo(1,2-b:5,4-b')-bi-4-pyron werden in 150 ml siedendem Alkohol gelöst und mit 24 g o-Aminophenol 2 Stunden am Rückfluss erhitzt. Nach Erkalten der Lösung saugt man, wenn nötig nach Einengung, die ausgefallenen Kristalle ab.orange needles, F = 3560 C (DMFA) UVmax: 461, 437, 276, 225 nm (dioxane) Analysis: Calc .: 62.86% C Found: 62.83 S C 3.84 S H 3.96% H 6.66% N 6.63% N 3- [6- (2-carboxylic acid ethyl ester-7-hydroxy-chromonyl) -acetylidene] -3,4-dihydro-2H-1,4-benzoxazin-2-one 35.8 g of 2,8-dicarbethoxy-benzo (1,2-b: 5,4-b ') - bi-4-pyrone are boiled in 150 ml Dissolved alcohol and refluxed with 24 g of o-aminophenol for 2 hours. After cooling down The precipitated crystals are filtered off with suction from the solution, if necessary after concentration.
Ausbeute: 80 % d.Th.Yield: 80% of theory
orangefarbene Nadeln, F = 3080 C (DMFA) UVmax: 460, 435, 277 nm (Dioxan) Analyse: Ber.: 62,71 % C Gef.: 62,91 % C 3,59 % H 3,50 % H 3,32 % N 3,32 % N 2,8-Di(N-hydroxyäthylcarbonsäureamid)-benzo(1,2-b:5,4-b')-bi-4-pyron 35,8 g 2,8 Dicarbäthoxy-benzo(1,2-b:5,4-b')-bi-4-pyron werden in 150 ml siedendem Alkohol gelöst und mit 13,44 g 2-Aminoäthanol 2 Stunden am Rückfluss erhitzt. Nach Erkalten der Lösung saugt man, wenn nötig nach Einengung, die ausgefallenen Kristalle ab.orange needles, F = 3080 C (DMFA) UVmax: 460, 435, 277 nm (dioxane) Analysis: Calc .: 62.71% C Found: 62.91% C 3.59% H 3.50% H 3.32% N 3.32% N 2,8-di (N-hydroxyethylcarboxamide) benzo (1,2-b: 5.4-b ') - bi-4-pyrone 35.8 g of 2.8 dicarbethoxy-benzo (1,2-b: 5,4-b ') - bi-4-pyrone are boiled in 150 ml Dissolved alcohol and refluxed for 2 hours with 13.44 g of 2-aminoethanol. To When the solution cools, the crystals which have precipitated out are suctioned off, if necessary after concentration away.
Ausbeute: 50 % d.Th.Yield: 50% of theory
gelbe Kristalle, F = 226° C (Äthanol) UVmax: 379, 289, 358 nm (Dioxan) Analyse: Ber.: 55,67 % C Gef.: 50,10 % C 4,15 % H 4,90 % H 7,21 % N 8,10 % N 4,6-Dihydroxy-benzo(1,2-b:5,4-b')-bipyrylium-perchlorat 21,42 g Benzo(1,2-b:5,4-b')-bi-4-pyron werden in 200 ml einer warmen Mischung von Essigsäure/Anhydrid (1:1) gelöst und mit 14,3 g 70 auger Perchlorsäure gerührt. Die nach kurzer Zeit ausfallenden Kristalle werden abgesaugt und getrocknet.yellow crystals, F = 226 ° C (ethanol) UVmax: 379, 289, 358 nm (dioxane) Analysis: Calc .: 55.67% C Found: 50.10% C 4.15% H 4.90% H 7.21% N 8.10% N 4,6-dihydroxy-benzo (1,2-b: 5,4-b ') - bipyrylium perchlorate 21.42 g of benzo (1,2-b: 5,4-b ') - bi-4-pyrone are in 200 ml of a warm mixture of Acetic acid / anhydride (1: 1) dissolved and stirred with 14.3 g of 70% perchloric acid. The crystals that precipitate out after a short time are filtered off with suction and dried.
Ausbeute: 30 % d.Th.Yield: 30% of theory
farblose Kristalle, F = 2730 C (Zersetzung) Analyse: Ber.: 34,72 % C Gef.: 41,86 % C 1,94 % H 2,81 % H Stufe A: Benzo(1,2-b:3,4-b':5,6-b"-tri-4-pyron 25,2 g 2,4,6-Triacetylphloroglucin werden mit 39,3 g N,N-Dimethylformamid-dimethylacetal in 350 ml siedendem absolutem Xylol 2 Stunden rückfliessend erhitzt und das entstehende Methanol dabei abdestilliert. Nach Erkalten saugt man den Niederschlag ab und kristallisiert um. Die Cyclisierung zum 4-Pyron erfolgt durch einstUndiges Erhitzen in 3 n Schwefelsäure bei 1000.colorless crystals, F = 2730 C (decomposition) analysis: calc .: 34.72% C Found: 41.86% C 1.94% H 2.81% H Grade A: Benzo (1,2-b: 3,4-b ': 5,6-b "-tri-4-pyrone 25.2 g of 2,4,6-triacetylphloroglucinol are mixed with 39.3 g of N, N-dimethylformamide dimethylacetal refluxed in 350 ml of boiling absolute xylene for 2 hours and the resulting Methanol distilled off in the process. After cooling, the precipitate is filtered off with suction and crystallized around. The cyclization to the 4-pyrone takes place by heating for one hour in 3N sulfuric acid at 1000.
Ausbeute: 65% d.Th.Yield: 65% of theory
farblose Kristalle, F >3600 C (Sublimation) Analyse: Ber.: 63,84 % C Gef.: 61,88 % C 2,14 % H 2,79 % H Stufe B: 1,3,5-Tri(pyrazol-3)-2,4,6-trihydroxy-benzol 5 g Benzo(1,2-b:3,4-b':5,6-b")-tri-4-pyron werden in 100 ml 80 einem wässrigem Hydrazinhydrat gelöst und 1 Stunde bei 1000 C gerührt. Dann wird mit 3 n Essigsäure versetzt, der Niederschlag aus Eisessig/Wasser oder 0,1 n Natronlauge umgefällt.colorless crystals, F> 3600 C (sublimation) Analysis: Calc .: 63.84 % C Found: 61.88% C 2.14% H 2.79% H Grade B: 1,3,5-tri (pyrazole-3) -2,4,6-trihydroxy-benzene 5 g of benzo (1,2-b: 3,4-b ': 5,6-b ") - tri-4-pyrone are dissolved in 100 ml of an aqueous hydrazine hydrate dissolved and stirred at 1000 ° C. for 1 hour. Then 3N acetic acid is added, the Precipitate from glacial acetic acid / water or 0.1 N sodium hydroxide solution.
Ausbeute: 50 % d.Th.Yield: 50% of theory
hellgelbe Kristalle, F = 360 C UVmax: 306 nm (Essigsäure) Analyse: Ber.: 55,56 % C Gef.: 52,20 % C 3,73 % H 3,80 % H 24,91 % N 23,4 % Nlight yellow crystals, F = 360 C UVmax: 306 nm (acetic acid) Analysis: Calc .: 55.56% C Found: 52.20% C 3.73% H 3.80% H 24.91% N 23.4% N
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722250377 DE2250377A1 (en) | 1972-10-13 | 1972-10-13 | 4,6-Disubst. resorcinol derivs - with e.g. psychopharmacological activity |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722250377 DE2250377A1 (en) | 1972-10-13 | 1972-10-13 | 4,6-Disubst. resorcinol derivs - with e.g. psychopharmacological activity |
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| Publication Number | Publication Date |
|---|---|
| DE2250377A1 true DE2250377A1 (en) | 1974-04-25 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722250377 Pending DE2250377A1 (en) | 1972-10-13 | 1972-10-13 | 4,6-Disubst. resorcinol derivs - with e.g. psychopharmacological activity |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2239263A1 (en) * | 2007-12-28 | 2010-10-13 | Sumitomo Chemical Company, Limited | Cyclic compound, its metal complex, and modified metal complex |
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1972
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2239263A1 (en) * | 2007-12-28 | 2010-10-13 | Sumitomo Chemical Company, Limited | Cyclic compound, its metal complex, and modified metal complex |
| EP2239263A4 (en) * | 2007-12-28 | 2011-07-06 | Sumitomo Chemical Co | Cyclic compound, its metal complex, and modified metal complex |
| US8546291B2 (en) | 2007-12-28 | 2013-10-01 | Sumitomo Chemical Company, Limited | Cyclic compound, its metal complex and modified metal complex |
| US9236613B2 (en) | 2007-12-28 | 2016-01-12 | Sumitomo Chemical Company, Limited | Cyclic compound, its metal complex and modified metal complex |
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