CS230342B1 - 1,9-dihydropyrolo-/l2,-acid hydrazide - Google Patents
1,9-dihydropyrolo-/l2,-acid hydrazide Download PDFInfo
- Publication number
- CS230342B1 CS230342B1 CS88283A CS88283A CS230342B1 CS 230342 B1 CS230342 B1 CS 230342B1 CS 88283 A CS88283 A CS 88283A CS 88283 A CS88283 A CS 88283A CS 230342 B1 CS230342 B1 CS 230342B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- carboxylic acid
- indole
- dihydropyrrolo
- furo
- methanol
- Prior art date
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- 239000002253 acid Substances 0.000 title claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- -1 heterocyclic nitrogen compounds Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 7
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 238000005259 measurement Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000003138 primary alcohols Chemical class 0.000 claims description 3
- 150000003333 secondary alcohols Chemical class 0.000 claims description 3
- 230000003595 spectral effect Effects 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- DZLFRQHFFVRYEE-UHFFFAOYSA-N 1h-indole-2-carbohydrazide Chemical compound C1=CC=C2NC(C(=O)NN)=CC2=C1 DZLFRQHFFVRYEE-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 238000000921 elemental analysis Methods 0.000 claims description 2
- ZXWUDCWRJHLBNL-UHFFFAOYSA-N ethyl 4h-furo[3,2-b]indole-2-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1C=C(C(=O)OCC)O2 ZXWUDCWRJHLBNL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000002329 infrared spectrum Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000012452 mother liquor Substances 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 2
- 238000005160 1H NMR spectroscopy Methods 0.000 claims 1
- KFHFDJDODKQNHH-UHFFFAOYSA-N N1C(=CC2=C1C=1NC3=CC=CC=C3C=1O2)C(=O)NN Chemical compound N1C(=CC2=C1C=1NC3=CC=CC=C3C=1O2)C(=O)NN KFHFDJDODKQNHH-UHFFFAOYSA-N 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 claims 1
- 235000021168 barbecue Nutrition 0.000 claims 1
- 239000002178 crystalline material Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- NKGUHSIMKXPTGH-UHFFFAOYSA-N 4h-furo[3,2-b]indole-2-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C=C(C(=O)O)O2 NKGUHSIMKXPTGH-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- PPWHTZKZQNXVAE-UHFFFAOYSA-N Tetracaine hydrochloride Chemical compound Cl.CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 PPWHTZKZQNXVAE-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000005077 diacylhydrazine group Chemical group 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Hydrazidy karboxylových kyselin možno pripraviť niekofkými sposobmi.The carboxylic acid hydrazides can be prepared in several ways.
Syntéza hydrazidov reakciou karboxylových kyselin s hydrazínom je najmenej vhodná metoda, lebo vyžaduje eliminovat z reakčného prostredia vodu. Nevýhoda přípravy hydrazidov z chloridov a anhydridov kyselin spočívá v tom, že bez ohl'adu na molárny poměr oboch reakčných komponentov produktom bývajú diacylhydrazíny. Za najvýhodnejšiu metodu sa pokládá příprava hydrazidov využitím esterov karboxylových kyselin ako východiskových látok. Z preparatívneho hiadiska bola táto reakcia preskúmaná už Curtiom a spolupracovníkmi [Chem. Ber. 35, 3229(1902)]. Prebytkom hydrazínu možno potlačit vznik N,N-diacylhydrazínu, ktorý vzniká ako vedlajší produkt reakcie.Synthesis of hydrazides by reaction of carboxylic acids with hydrazine is the least suitable method since it requires the elimination of water from the reaction medium. A disadvantage of the preparation of hydrazides from chlorides and acid anhydrides is that, regardless of the molar ratio of the two reaction components, the product is diacylhydrazines. The most preferred method is the preparation of hydrazides using carboxylic acid esters as starting materials. From a preparatory point of view, this reaction has already been investigated by Curti and co-workers [Chem. Ber. 35, 3229 (1902)]. Excess hydrazine can suppress the formation of N, N-diacylhydrazine, which is formed as a by-product of the reaction.
Stúdiom literatury sa ukázalo, že hydrazid kyseliny l,9-dihydropyrolo[2‘,3‘:4,5]furo[3,2-b]indol-2-karboxylovej nebol doteraz připravený.A literature study has shown that 1,9-dihydropyrrolo [2,3-b] furo [3,2-b] indole-2-carboxylic acid hydrazide has not been prepared.
Predmetom vynálezu je hydrazid kyseliny 1,9-dihydropyrolo [ 2‘,3‘:4,5 ] furo'[ 3,2-b ] indol-2-karboxylovej vzorca IThe present invention provides 1,9-dihydropyrrolo [2,3-b: 4,5] furo [3,2-b] indole-2-carboxylic acid hydrazide of formula I
(I ) a sposob jeho přípravy.(I) and the method of its preparation.
Podstata sposobu přípravy hydrazidu kyseliny l,9-dihydropyrolo[2‘,3‘:4,5)furo[ 3,2-b]indol-2-karboxylove] spočívá v tom, že sa na etylester kyseliny 1,9-dihydropyrolo [ 2‘,3‘: 4,5 ]furo[ 3,2-b ] indol-2-karboxylovej (Čsl. aut. osvědč. 193 130) vzorca IIThe process for the preparation of 1,9-dihydropyrrolo [2 ', 3': 4,5) furo [3,2-b] indole-2-carboxylic acid] hydrazide is based on the formation of 1,9-dihydropyrolo [ethyl] ester [ 2 ', 3': 4,5] furo [3,2-b] indole-2-carboxylic acid (Cz. Aut. Certificate 193 130) of formula II
(lit pósobí hydrazínhydrátom v metanole, etanole alebo vyšších primárných alebo sekundárných alkoholoch pri teplote varu rozpúšťadla.(lit with hydrazine hydrate in methanol, ethanol or higher primary or secondary alcohols at the boiling point of the solvent.
Výhody sposobu přípravy zlúčeniny podlá vynálezu spočívajú okrem iného v tom, že sa reakcia uskutočňuje v nenáročných podmienkach s dobrými výťažkami.The advantages of the process for the preparation of the compound according to the invention are, inter alia, that the reaction is carried out under undemanding conditions with good yields.
Hydrazidy karboxylových kyselin majú široké použitie ako rožne reakčné komponenty v organické] syntéze. S kyselinou dusitou dávajú azidy, ktoré poskytujú širokú paletu reakcii. Reagujú s kyselinami, halogenidmi kyselin, nitrilmi a pod. Poskytujú možnost přípravy róznych heterocyklických dusíkových zlúčenín s dvomi, připadne i viacerými dusíkovými heteroatómami.The carboxylic acid hydrazides have wide application as various reaction components in organic synthesis. With nitrous acid they give azides which provide a wide variety of reactions. They react with acids, acid halides, nitriles and the like. They provide the possibility of preparing different heterocyclic nitrogen compounds with two or more nitrogen heteroatoms.
Predmet vynálezu ilustrujú, ale neobmedzujú následovně příklady:The invention is illustrated but not limited by the following examples:
Příklad 1Example 1
Hydrazid kyseliny 1,9-dihydropyrolo[2‘,3‘:4,5.]furo;[3,2-bjindol-2-karboxylovej.1,9-Dihydropyrrolo [2,3-d: 4,5] furo [3,2-b] indole-2-carboxylic acid hydrazide.
Etylester kyseliny 1,9-dihydropyrolo[ 2 ‘, 3:4,5 ] fůro [ 3,2-b ] indol-2-karboxylovej (2,68 g, 0,01 mol) sa rozpustí v metanole (200 ml] a přidá sa 90 %-ný hydrazínhydrát (3,5 ml). Zmes sa zahrieva pri teplote varu počas 10 h. Potom sa část rozpúšťadla oddestiluje (100 ml), reakčná zmes sa ochladí, krystalická látka sa odfiltruje. Získá sa hydrazid kyseliny 1,9-dihydropyrolo[ 2‘,3‘ :4,5 ] fůro [ 3,2-b) indol-2-karboxylove) vDissolve 1,9-dihydropyrrolo [2 ', 3: 4,5] furo [3,2-b] indole-2-carboxylic acid ethyl ester (2.68 g, 0.01 mol) in methanol (200 mL) and 90% hydrazine hydrate (3.5 ml) is added and the mixture is heated at boiling for 10 h. After part of the solvent is distilled off (100 ml), the reaction mixture is cooled, the crystalline substance is filtered off to give acid hydrazide 1, 9-dihydropyrrolo [2 ', 3': 4,5] furo [3,2-b] indole-2-carboxylic acid
76,5 % výtažku.76.5% yield.
Příklad 2Example 2
Etylester kyseliny 1,9-dihydropyrolo[ 2‘,3‘:4,5 ]furo.[ 3,2-b! indol-2-karboxylovej (2,68 g, 0,01 mol) a 90 %-ný hydrazínhydrát (3,5 ml) sa přidá k matečnému roztoku získanému po odfiltrovaní hydrazidu kyseliny 1,9-dihydropyrolo [ 2 ‘, 31:4,5 ] fůro [ 3,2-b j indol-2-karboxylovej. Reakčná zmes sa zahrieva1,9-Dihydropyrrolo [2 ', 3': 4,5] furo [3,2-b] ethyl ester; indole-2-carboxylic acid (2.68 g, 0.01 mol) and 90% hydrazine hydrate (3.5 mL) are added to the mother liquor obtained after filtering 1,9-dihydropyrrolo [2 ', 3 L] hydrazide: 4,5] furo [3,2-b] indole-2-carboxylic acid. The reaction mixture is heated
h. Další postup je analogický ako v příklade 1.h. The further procedure is analogous to Example 1.
Výťažok 81,3 %.Yield 81.3%.
Příklad 3Example 3
Postup je analogický s príkladom 1, ale miesto metanolu sa použije etanol. Reakčná zmes sa zahrieva 8 h. a spracuje sa ako v příklade 1.The procedure is analogous to Example 1, but ethanol is used instead of methanol. The reaction mixture was heated for 8 h. and processed as in Example 1.
Získaný hydrazid kyseliny 1,9-dihydropyrolo [ 2‘ ,3 ‘: 4,5 j f uroj[ 3,2-b ] indol-2-karboxylovej (I) je zlúčenina štruktúrneho vzorca:The obtained 1,9-dihydropyrrolo [2 ‘, 3‘: 4,5 µfuro [3,2-b] indole-2-carboxylic acid hydrazide (I) is a compound of the structural formula:
Zlúčenina I je krystalická až 226 °C (etanol).Compound I is crystalline up to 226 ° C (ethanol).
Sumárny vzorec: CisHioNiOž Molekulová hmotnost: 253,3Summary formula: C18H10NiO2 Molecular Weight: 253.3
NHNHZ (I ) látka, t. t. 224NHNH Z (I) m.p. 224
trálnymi metodami IC, XH NMR.tral by IR, NMR X.
IČ: vmax (KBr cm1): 1611 (C=O), 3285 (NH) XH NMR: (DMSO—dej: 6,96 (1H, s, C(3)—H),IR: v max (KBr cm 1): 1611 (C = O), 3285 (NH) x H NMR: (DMSO-put: 6.96 (1 H, s, C (3) H);
7,00—7,75 (4H, m, Haionl)7.00-7.75 (4H, m, H aionl)
Spektrálné meraniaSpectral measurements
Infračervená spektra sa namerali na spektrofotometr! SPECORD 71 IR (Carl Zeiss Jena). ]HNMR spektra boli namerané na 80 MHz spektroíotometrl BS 487 C Tesla. Pri meraní sa použil vnútorný standard tetrametylsilán.Infrared spectra were recorded on a spectrophotometer! SPECORD 71 IR by Carl Zeiss Jena. ] H NMR spectra were recorded at 80 MHz spektroíotometrl Tesla BS 487 C. The internal standard tetramethylsilane was used in the measurement.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS88283A CS230342B1 (en) | 1983-02-09 | 1983-02-09 | 1,9-dihydropyrolo-/l2,-acid hydrazide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS88283A CS230342B1 (en) | 1983-02-09 | 1983-02-09 | 1,9-dihydropyrolo-/l2,-acid hydrazide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS230342B1 true CS230342B1 (en) | 1984-08-13 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS88283A CS230342B1 (en) | 1983-02-09 | 1983-02-09 | 1,9-dihydropyrolo-/l2,-acid hydrazide |
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| Country | Link |
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| CS (1) | CS230342B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110407854A (en) * | 2018-08-17 | 2019-11-05 | 北京加科思图新药研发有限公司 | New tetracyclic compound |
-
1983
- 1983-02-09 CS CS88283A patent/CS230342B1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110407854A (en) * | 2018-08-17 | 2019-11-05 | 北京加科思图新药研发有限公司 | New tetracyclic compound |
| CN110407854B (en) * | 2018-08-17 | 2020-09-15 | 北京加科思新药研发有限公司 | Novel tetracyclic compounds |
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