DE1443336A1 - Process for the preparation of furan and pyran derivatives - Google Patents
Process for the preparation of furan and pyran derivativesInfo
- Publication number
- DE1443336A1 DE1443336A1 DE19611443336 DE1443336A DE1443336A1 DE 1443336 A1 DE1443336 A1 DE 1443336A1 DE 19611443336 DE19611443336 DE 19611443336 DE 1443336 A DE1443336 A DE 1443336A DE 1443336 A1 DE1443336 A1 DE 1443336A1
- Authority
- DE
- Germany
- Prior art keywords
- furan
- acid
- preparation
- triple bond
- derivatives
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or 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 to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren sur Herstellung von Puran-und Pyran-Derivaten.Process for the production of purane and pyran derivatives.
Es wurde gefunden, daß Substanzen (1), die eine enolisierbare Carbonylgruppe in y-Stellung zu einer Dreifachbindung enthalten, h mit geringen Mengen vcn Zinkearbonat, conc.It has been found that substances (1) having an enolizable carbonyl group contained in y-position to a triple bond, h with small amounts of zinc carbonate, conc.
Schwefelsäure bzw. conc. Phosphorsäure bei Zimmertemperaur in ungesättigte cyclische Ather (II oder III) überführen lassen. Derartige Alkin-Ketone sind u. a. darstellbar durch @ eince Alkin-2-yl-(1)-Restes in ß-Dicarbonyl-Yerbindungen. tta R2 = CH3; R3 = OC2H5 IIb R2 = CH3; R3 = CH3 IIe R2 C6Hs ß 2H5 IId R2 = C6H5; R3 = CH3 So wntateht s B. aus Propinylacetessigester (I Ri 0 H ; R2 a CH3; R3 = OC2H5) der 2,5-Dimethylfurancarbonsäure-3-aux (IIa), aus propinylacetylaceton (I: R1 = H; R2 n CH3; R3 = CH3) 2,5-Dimethyl-3-acetylfuran. (IIb). Aus Propinylbenzoylessigester (I: R1 = H; R2 = C6H5; R3 = OC2H5) E 6S iCH. 8'A YLbtaJ. °criL3"d. rFIC » . r°"'u. Cl. de V (IIc), aus @ro@inuylbenzcylaceton (R1 = H; R2 = C6H5; R3 = CH3) das 5-Methyl-3-acetyl-2-phenyl-furan (IId). let die Acetylentindun@ @ nicht endständig (I: R1 = Aryl oder Alkyl), so entstehen die analogen y-Pyan-Derivate (III).Sulfuric acid or conc. Let phosphoric acid be converted into unsaturated cyclic ethers (II or III) at room temperature. Such alkyne ketones can be represented, inter alia, by a single alkyne-2-yl (1) radical in ß-dicarbonyl compounds. tta R2 = CH3; R3 = OC2H5 IIb R2 = CH3; R3 = CH3 IIe R2 C6Hs ß 2H5 IId R2 = C6H5; R3 = CH3 This is how it becomes possible, for example, from propynyl acetic acid ester (I Ri 0 H; R2 a CH3; R3 = OC2H5) of 2,5-dimethylfurancarboxylic acid-3-aux (IIa), from propynyl acetylacetone (I: R1 = H; R2 n CH3 ; R3 = CH3) 2,5-dimethyl-3-acetylfuran. (IIb). From propynyl benzoyl acetic ester (I: R1 = H; R2 = C6H5; R3 = OC2H5) E 6S iCH. 8'A YLbtaJ. ° criL3 "d. RFIC». R ° "'u. Cl. de V (IIc), from @ ro @ inuylbenzcylaceton (R1 = H; R2 = C6H5; R3 = CH3) 5-methyl-3-acetyl-2-phenyl-furan (IId). If the acetylenedine @ @ is not terminal (I: R1 = aryl or alkyl), the analogous y-pyan derivatives (III) are formed.
Steht der Alkinuyl-Rest in o-Stellung zu einer enolisierbaren Carbonyle ppe in einer alicyclischen oder heterocyclische Yrbladunj o so läßt sich der Furan-Ring bzw. der y-Pyran- Mag water den gleiche Bedingungen herstellen; es entstehen kondensierte Pwr. n- bzw. y-@yran-Derivate.If the alkinuyl radical is in the o-position to an enolizable carbonyl ppe in an alicyclic or heterocyclic Yrbladunj o so can the furan ring or the y-pyran Mag water create the same conditions; condensed Pwr arise. n- or y- @ yran derivatives.
Aut i<w<Mtwlßtwichau*dMrropinylcyclohwxandion IV: R1 = H) das 2,3-(2'-Methylfurano)-cyclohexen-2-on-(1) (V) gewinnen, und aus den Phenylpropinylcyclohexandion (IV: R1 = C6H5) entateht das 2,3-(2'-@henylpyrano)-cyclohexen-2-on-tl) ( 3-Propinyl-4-hy@roxypyrone-(2) (VII), die nach K. H.Aut i <w <Mtwlsstwichau * dMrropinylcyclohwxandione IV: R1 = H) to obtain the 2,3- (2'-methylfurano) -cyclohexen-2-one- (1) (V), and from the phenylpropinylcyclohexanedione (IV: R1 = C6H5 ) contains the 2,3- (2 '- @ henylpyrano) -cyclohexen-2-one-tl) ( 3-propynyl-4-hy @ roxypyrone- (2) (VII), which according to KH
B o l t s 0 und ri. H. H w 1 d e n b 1 u t h (Chem. Ber.B o l t s 0 and ri. H. H w 1 d e n b 1 u t h (Chem. Ber.
91, 2849 91, 1958)) aus ropinyl@slonsäuredichlorid (VIII) und Acetessigester (@ : R1 = CH3; R2 = CO2H5), Benz@iessigester (IX: R1 = C6H5; R2 = OC2H5), Acetylaceton (IX: R1 = CH3; R2 = CH3), Benzoylaceton (IX: R1 = C6H5; R2 = CH3) zugänglich wind, nrn untor dn oben angeführten Bedingungen in die @ zugehörigen 3,4-(2-Methylfurano)-pyrone-(2) (x) überfuhrt werden. 91, 2849 91, 1958)) from ropinyl @ sonsic acid dichloride (VIII) and acetoacetate (@: R1 = CH3; R2 = CO2H5), benz @ acetic ester (IX: R1 = C6H5; R2 = OC2H5), acetylacetone (IX: R1 = CH3; R2 = CH3), benzoylacetone (IX: R1 = C6H5; R2 = CH3) is accessible, under the conditions listed above in the corresponding 3,4- (2-methylfurano) -pyrone- (2) (x) be transferred.
Diw Monopropinylbarbitursäure (XI: R1 = H) geht unter den gleichen Bedingungen in das 5,6-(2'-Methylfurano)-uracil (XII) Uber. Aua der henylpropinylbarbitursäure (XI: R = C6H5) entateht das 5,6-(2-Phenylpyrano)-uracil. (XIII). Diw monopropynylbarbituric acid (XI: R1 = H) is converted into 5,6- (2'-methylfurano) uracil (XII) under the same conditions. The 5,6- (2-phenylpyrano) uracil is also present in the phenylpropynylbarbituric acid (XI: R = C6H5). (XIII).
In analoger @eise läßt sich aus der Monopropinylthiobarbitursäure das 5,6-(2'-Methylfurano)-thiouracil daratellen.In an analogous manner, from monopropynylthiobarbituric acid the 5,6- (2'-methylfurano) -thiouracil represent.
Die 6-Hydroxy-5-propinyl-pyrimidine (XIV), die aus Amidinen (XV) und 2-prpinyl-substituierten ß-Ketonsäuresstern (XVI) zuganglich zind, gehen ebenfalle diese Cyclisierungs-Reaktion in en entstehen die 5,6-(2'-Methylfurano)-pyrimidine (XVII). The 6-hydroxy-5-propynyl-pyrimidines (XIV), which are accessible from amidines (XV) and 2-propynyl-substituted ß-ketonic acid star (XVI), also go into this cyclization reaction in en the 5,6- ( 2'-methylfurano) pyrimidines (XVII).
Di auf diesem @ege zugänglichen Subetansen sind als Zwischenstufen zur Synthese von Arsneistoffen brauchbar; z.T. zeichnen sie sich durch be@erkenswerte pharsakologische Eigenschaften aus, wie z. B. das Kethylfuranouracil. Das Methylfuranouracil und ebenso das Pyranouracil bzw. die Furanopyrimidene besitsen Lösungsvermittler-Eigenschaften gwgtnüber iyramidon, da in Gogenwart durer Substanzen bis über 40 % in Lösung geht.The subetanses accessible on this @ege are as intermediate stages useful for the synthesis of arsenic materials; some of them are noteworthy pharsacological properties such as B. the Kethylfuranouracil. The methylfuranouracil and also the pyranouracil or the furanopyrimidenes possess solubilizer properties gwgtn about iyramidon, since in Gogenwart durer substances go into solution up to 40%.
Beispiel 1 2,5-Dimethyl-furen-earbonsäure-3-sethylester 3 g Propargylacetessigester werden in einem 10 ml Spitzkolben sit Rückflußkühler mit 30 mg Zinkearbonat im Ölbad auf 150°C erwärmt. @@ setzt eine exotherma Reaktion ein; zur Vervollständigung der Umsetzung wird noch eine halbe Stunde aut 1800 erwärmt. Der entstandene 2,5-Dimethyl-furan-@arbonsäure-3-asthylester wird im Vakuum abdestilliert.Example 1 2,5-dimethyl-furen-carboxylic acid-3-ethyl ester 3 g propargyl acetic acid ester are heated to 150 ° C. in a 10 ml pointed flask sit reflux condenser with 30 mg zinc carbonate in an oil bath. @@ starts an exothermic reaction; to complete the reaction, it is heated to 1800 for another half hour. The resulting 2,5-dimethyl-furan-@arboxylic acid 3-asthyl ester is distilled off in vacuo.
229S-10.Ausbeute2,3g(77%d.Th.).229S-10. Yield 2.3 g (77% of theory).
Nit der nach C. Paal (Ber. Dtsch. Chem. Ges. 17, 2765 765 (1884)) aus @@etonylacetessigester dargestellten Verbindung zeigt die durch Verseifung erhaltene 2,5-Dimethylfurancarbansäure -(3) keine Schmelzpunktsdepression.According to C. Paal (Ber.Dtsch. Chem. Ges. 17, 2765 765 (1884)) from @@ etonylacetoacetic ester shows the compound obtained by saponification 2,5-dimethylfurancarboxylic acid - (3) no melting point depression.
Fp 135°.M.p. 135 °.
Unter den gleichen Versuchsbedingungen,wie in Beispiel 1 beschrieben, Ias@@n sich die nachfolgenden Beispiele 2,3,6 und 10 darstellen.Under the same test conditions as described in Example 1, The following examples 2, 3, 6 and 10 are presented.
Beispiel 2 2,5-Dimethyl-3-acetyl-furan AM 5 g propargylacetylaceton und 25 w ZinkMrbonat entstehen 3,8 g (= 76 @ d. Th.) 2,5-Dimethyl-3-acetylfuran.Example 2 2,5-dimethyl-3-acetyl-furan AM 5 g propargylacetylacetone and 25 w zinc carbonate give 3.8 g (= 76 @ d. Th.) 2,5-dimethyl-3-acetylfuran.
Kp20 90-920, w 3 5-Methyl-2-pheryl-f@ran-carbora@ure -3-äthlester Aus 5 g Propargylbenzoylenssigester und 50 mg Zinkearbonat entstehen 3, 6 g (= 72 % d. Th.) 5-Methyl-2-phenyl-furanowrboaaure-'thylostex'*Kp.88-19°.Bp 20 90-920, w 3 5-methyl-2-pheryl-f @ ran-carbora @ ure -3-ethyl ester From 5 g of propargyl benzoyl ester and 50 mg of zinc carbonate, 3.6 g (= 72% of theory) of 5-methyl-2-phenyl-furano-acid 'thylostex' * boiling point 88-19 ° are formed.
Die freie Säure aus diesem @ster zeigt mit der nach W. B o ra che und A. els (Ser. Dtsch. Chem. Ges. 39, 1923 (1927)) aus Benzoylacetessigester dargestellten Verbindung koinê Schmelspunktsdepression. Fp. 147°. pile 4 2-Methyl-3-acetyl-6-phenylpyran-(2) 3g rhenylpropargylaoetylrQeton werden in 5 one. $chw azure gelöst und dieseLüwucnachkurMB:StehenbeiSHemertemperatur auf zerkleinertas @is gegossen. Das ausfallende Kristallisat schmilzt nach Reinigung (Ligroin) bei Fp 89°.The free acid from this ester shows, with the compound prepared from benzoylacetoacetic ester according to W. B o ra che and A. els (Ser. Dtsch. Chem. Ges. 39, 1923 (1927)), melting point depression. M.p. 147 °. pile 4 2-methyl-3-acetyl-6-phenylpyran- (2) 3g of rhenylpropargylaoetylrQeton are in 5 ones. $ chw azure dissolved and this LuwucnachkurMB: standing at the temperature of the hemisphere poured onto shredded tas @is. The precipitated crystals melt after purification (ligroin) at melting point 89 °.
Ausbeute: 2,1 g (= 70 d. Th.) 2-Methyl-3-acetyl-6-phenylpyran-(2).Yield: 2.1 g (= 70 of theory) of 2-methyl-3-acetyl-6-phenylpyran- (2).
Beispiel 5 2,3-(2'-Methylfurano)-cyclochexen-2-on-(1) Bei dem Versuch, aus 22g Cyclohexandion-(1,3),4,5 g Natrium und 23,8 g Propargylbromid nach B. Stetter und . D 9 r i a h @ (Chem. Ber. 85, 61, 290, 1061, (1952)) da 2-Propinylcyclochexandion-(1,3) darzustellen, trat während der Aufabeitung des Ansatses bei d*m Ansaurern mit Schwefelsciure schen Cyclisierung ein. Es wurdenneben dem 3-Propinyl-Äther de Cycohexen-2-on-(1) 4,2 g (-14, 7 % d. Th.) 2, 3- (2'-Methylfurano)-cyclohexen-2-on-(1), Fp. 73-75°, erha} i l 6 2,3-(2'-Phenylpyrano)-cyclohexen-2-on(1) Au 2, 1 g 2-(Phonylpropargyl)-cyclohexandion-(1,3) und 25 mg Zinkeaybonat werden in dor gleichen Reise,wie bei Beispiel 1 beschrieben, 0,29g (= 13,5 % d. Th.) 2,3-(2'-Phenylpyrano)-cyclohexen-2-on-(1) erhalten. Fp. 122-124°.Example 5 2,3- (2'-Methylfurano) -cyclochexen-2-one- (1) In the attempt to make from 22 g of cyclohexanedione- (1.3), 4.5 g of sodium and 23.8 g of propargyl bromide according to B. Stetter and. D 9 riah @ (Chem. Ber. 85, 61, 290, 1061, (1952)) because 2-propynylcyclochexanedione- (1,3) occurred during the preparation of the preparation in the case of acidification with sulfuric acid cyclization. In addition to the 3-propynyl ether de Cycohexen-2-one- (1) 4.2 g (-14.7% of theory) 2,3- (2'-methylfurano) -cyclohexen-2-one- (1), m.p. 73-75 °, obtainable 6 2,3- (2'-phenylpyrano) -cyclohexen-2-one (1) Au 2, 1 g of 2- (Phonylpropargyl) -cyclohexanedione- (1,3) and 25 mg of zinc acetate are in the same trip as described in Example 1, 0.29 g (= 13.5% of theory) 2, 3- (2'-Phenylpyrano) -cyclohexen-2-one- (1) obtained. 122-124 °.
BisDil 7 3,4-(2'-Methylfurano)-5-earbaethoxy-6-phenylpyron-(2) 5 @ 3-@roparyl-4-hydroxy-5-carbasthoxy-6-phenylpyron- (2) werden in *one* hosph@@äure gelöst und diese ung nach kursen Stehen auf serkletnertes Et gegossen. Die ausfallondo kristallina Verbindung sch@ilst nach dem Reinigen bei Fp 158°. AuwbwuKt3e(60%d.Th.)3,4-(2'-ethylfurano)-5-carbaethoxy-6-phenylpyron-(2).BisDil 7 3,4- (2'-methylfurano) -5-earbaethoxy-6-phenylpyrone- (2) 5 @ 3- @ roparyl-4-hydroxy-5-carbasthoxy-6-phenylpyrone- (2) are dissolved in * one * phosph @@ acid and after the course this oil is poured onto a clay sheet. The ausfallondo crystalline compound shocks after cleaning at m.p. 158 °. Growth (60% of theory) 3,4- (2'-ethylfurano) -5-carbaethoxy-6-phenylpyrone- (2).
Beispiel @ 4,5-(2'-Methylfurano)-uracil 16,6 g 5-Propargylbarbituräure werden in 150 ml cono.Example @ 4,5- (2'-Methylfurano) -uracil 16.6 g of 5-propargylic barbituric acid are added to 150 ml of cono.
Schwefelsäure gelöst und diese Lösung anschließend auf Eis gegossen. Bie gereinigte gte Kristalline Verbindung schmilzt bei Fp 268°. Ausbeute: 9 g (= 49 % d. Th.) 4,5-(2'-Methylfurano)-uracil. Beispiel 9 5,6-(2'-Phenylpyrano)-uracil Aus 6,0 g 5-(3-Phenyl@ropin-2-yl)-barbitursäure und 30ml cone, Schwefelsäure werden unter den in Beispiel 8 beschriebcnwn Versuchsb@@ingungen 5,5 g (= 80 @ d. Th.) 5,6(2'-Phenylprano)-urneil erhalten, Fp. 187°.Dissolved sulfuric acid and then poured this solution onto ice. The purified crystalline compound melts at mp 268 °. Yield: 9 g (= 49% of theory) 4,5- (2'-methylfurano) -uracil. Example 9 5,6- (2'-Phenylpyrano) uracil From 6.0 g of 5- (3-phenyl @ ropin-2-yl) barbituric acid and 30 ml of cone, sulfuric acid, 5.5 g (= 80% of theory) of 5 are obtained under the experimental procedures described in Example 8 , 6 (2'-phenylprano) umeil obtained, mp. 187 °.
Beispiel 10 2, 4-Dime thyl-5,6-(2'-methylfurano)-pyrimidin Aus 2 g 2,4-Dimothyl-5-propargyl-pyrimidon-(6) und 25 mg Zinkearbonat werden nach den in Beispiel 1 beschriebenen Versuchsbeidingungen 1,3 g (= 63 % d. Th.) 2,4-Dimethyl-5,6-(2'-Methylfurano)-pyrimidin erhalten.Example 10 2,4-Dimethyl-5,6- (2'-methylfurano) -pyrimidine From 2 g of 2,4-dimothyl-5-propargyl-pyrimidone- (6) and 25 mg of zinc carbonate, 1.3 g (= 63% of theory) of 2,4-dimethyl-5 are obtained according to the test conditions described in Example 1 , 6- (2'-methylfurano) pyrimidine obtained.
- Patentansprüche -- patent claims -
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC029541 | 1961-04-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1443336A1 true DE1443336A1 (en) | 1969-11-27 |
Family
ID=7431461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19611443336 Pending DE1443336A1 (en) | 1961-04-13 | 1961-04-13 | Process for the preparation of furan and pyran derivatives |
Country Status (1)
| Country | Link |
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| DE (1) | DE1443336A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4487626A (en) * | 1980-08-22 | 1984-12-11 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
-
1961
- 1961-04-13 DE DE19611443336 patent/DE1443336A1/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4487626A (en) * | 1980-08-22 | 1984-12-11 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
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