CS240394B1 - 1-acetylbenzo(b) furo (3,2-b) pyrrole and method of its preparation - Google Patents
1-acetylbenzo(b) furo (3,2-b) pyrrole and method of its preparation Download PDFInfo
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- CS240394B1 CS240394B1 CS847850A CS785084A CS240394B1 CS 240394 B1 CS240394 B1 CS 240394B1 CS 847850 A CS847850 A CS 847850A CS 785084 A CS785084 A CS 785084A CS 240394 B1 CS240394 B1 CS 240394B1
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- Czechoslovakia
- Prior art keywords
- furo
- pyrrole
- acetylbenzo
- preparation
- benzo
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 9
- PLJIVNLEQUBQTH-UHFFFAOYSA-N 4h-furo[3,2-b]pyrrole Chemical compound O1C=CC2=C1C=CN2 PLJIVNLEQUBQTH-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- 125000005605 benzo group Chemical group 0.000 claims description 7
- JMFBVKJFJONNGQ-UHFFFAOYSA-N 4h-furo[3,2-b]pyrrole-2-carboxylic acid Chemical compound N1C=CC2=C1C=C(C(=O)O)O2 JMFBVKJFJONNGQ-UHFFFAOYSA-N 0.000 claims description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 7
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HERVOAMWSLDMKE-UHFFFAOYSA-N 2h-furo[3,2-b]azepine Chemical class C1=CC=NC2=CCOC2=C1 HERVOAMWSLDMKE-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- -1 Nitrogen-containing heterocyclic compounds Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- ULEQQHNPISCAPV-UHFFFAOYSA-N ethyl 2-(4-chlorophenyl)-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound C=1C=2NC(C(=O)OCC)=CC=2OC=1C1=CC=C(Cl)C=C1 ULEQQHNPISCAPV-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Vynález sa týká l-acetylbenzo[h]furo[3,2-b] pyrolu a spósobu jeho přípravy. Vhodnou metodou na jeho přípravu, je dekarboxylačná acetylácia kyseliny benzo[b]furo[3,2-b]pyrol-2-karboxylovej.The invention relates to 1-acetylbenzo [h] furo [3,2-b] pyrrole and a process for its preparation. A suitable method for its preparation is the decarboxylation acetylation of benzo [b] furo [3,2-b] pyrrole-2-carboxylic acid.
Všeobecne dekarboxylácia karboxylových kyselin představuje jednoduchá reakciú, ktorú možno uskutočniť viacerými postupmi. Výběr metódy ovplyvňuje najma štruktúra východiskové]' kyseliny, jej fyzikálno-chemické vlastnosti, ako aj fyzikálně a chemické vlastnosti očekávaného produktu. Vačšina dekarboxylačných reakcii sa realizuje v kvapalnej fáze bez katalyzátora, alebo v přítomnosti homogenného či tuhého katalyzátora.Generally, the decarboxylation of carboxylic acids is a simple reaction that can be accomplished in a number of ways. The choice of method influences in particular the structure of the starting acid, its physicochemical properties as well as the physical and chemical properties of the expected product. Most of the decarboxylation reactions are carried out in the liquid phase without catalyst, or in the presence of a homogeneous or solid catalyst.
Dusíkové heterocyklické zlúčeniny s NH vazbou napr. pyrol, indol alebo karbazol sa alkylujú alebo acylujú vo formě aniónu generovaného ich reakciou so silnou zásadou, ako je napr. amid sodný, hydrid litný alebo organokovy. V literatuře sú opísané alkylácie pyrolu [Heany H., Ley J.: J. Chem. Soc. Perkin Trans 2 292 (1972),' Garner E.‘, Albisser J.: Chemistry and Industry 110 (1974)]. Acetyláciu 2-(4-chlórfenyl)-5-etoxykarbonyl-furo[3,2-b] pyrolu cestou N-lítnej soli sme popínali v náročných reakčných podmlenkach [Krutošíková A., Kováč J., Chudobová M., Ilavský D., Collection Czechoslov. Chem. Commun. 45, 2 949 (1980)].Nitrogen-containing heterocyclic compounds with an NH bond e.g. pyrrole, indole or carbazole are alkylated or acylated in the form of an anion generated by their reaction with a strong base, such as e.g. sodium amide, lithium hydride or organometals. The alkylations of pyrrole have been described in the literature [Heany H., Ley J .: J. Chem. Soc. Perkin Trans 2292 (1972), Garner E., Albisser J .: Chemistry and Industry 110 (1974)]. Acetylation of 2- (4-chlorophenyl) -5-ethoxycarbonyl-furo [3,2-b] pyrrole via the N-lithium salt has been described in challenging reaction conditions [Krutošíková A., Kováč J., Chudobová M., Ilavský D., Collection Czechoslov. Chem. Commun. 45, 2949 (1980)].
Štúdium literatúry ukázalo, že 1-acetylbenzo [b] fůro [3,2-b] pyrol nebol doteraz připravený.A literature study has shown that 1-acetylbenzo [b] furo [3,2-b] pyrrole has not been prepared yet.
Predmetom vynálezu je 1-acetylbenzo[b]furo[3,2-b]pyrol vzorca IThe present invention provides 1-acetylbenzo [b] furo [3,2-b] pyrrole of formula I
a spósob jeho přípravy.and a method for preparing it.
Podstata spósobu přípravy 1-acetylbenžo[b]furo[ 3,2-b] pyrolu vzorca I spočívá v tom, že sa kyselina benzo[b]furo[3,2-b]pyrol-2-karhoxylová vzorca IIThe essence of the process for the preparation of 1-acetylbenzo [b] furo [3,2-b] pyrrole of formula I is that benzo [b] furo [3,2-b] pyrrole-2-carboxylic acid of formula II
(IH zahrieva v acetanhydride pri teplotách 110 až 136 °C.(IH is heated in acetic anhydride at 110-136 ° C).
Výhody spósobu přípravy zlúčeniny I podlá vynálezu spočívajú okrem iného v tom, že sa reakcia dekarboxylácie a súčasne] acetylácie uskutočňuje v jednom stupni v nenáročných podmienkach s dobrým výťažkom, pričom sa získá stabilizovaný 1-acétylbenzo(b) fůro) 3,2-b] pyrol.Advantages of the process for the preparation of the compound I according to the invention are, inter alia, that the decarboxylation reaction and the acetylation reaction are carried out in one step under undemanding conditions in good yield, to obtain stabilized 1-acetylbenzo (b) furo 3,2-b] pyrrole.
Predmet vynálezu ilustrujú, ale neobmedzujú následovně příklady:The invention is illustrated but not limited by the following examples:
PřikladlEXAMPLE
Kyselina benzo [ b ] fůro [ 3,2-b ] pyr ol-2-karboxylová (1,5 g, 0,0008 mol) a acetanhydrid (20 ml) se refluxuje za miešania 4 h. Reakčná zmes sa za horúca přefiltruje, roztok sa zahustí a po ochladení vylúčený surový produkt I sa odsaje a prekryštalizuje. Výťažok 1 g (66 %), t. t. 101 °C (etanol). Pre C12H9NO2 (199,2) vypočítané 7,03 % N, nájdené 7,30 % N.Benzo [b] furo [3,2-b] pyrrole-2-carboxylic acid (1.5 g, 0.0008 mol) and acetic anhydride (20 mL) were refluxed with stirring for 4 h. The reaction mixture is filtered while hot, the solution is concentrated and, after cooling, the precipitated crude product I is filtered off with suction and recrystallized. Yield 1 g (66%), m.p. t. 101 [deg.] C. (ethanol). For C12H9NO2 (199.2) calculated 7.03% N, found 7.30% N.
Štrpktúra zlúčeniny I bola dokázaná spektrálnými metodami: IR, UV, XH NMR.Štrpktúra Compound I showed the spectral methods: IR, UV, X H NMR.
IR (CHCI3, cm1): v (C=O) = 1716 UV (metanol, nm): 253 (4,40, 307 (4,17) Příklad 2IR (CHCl 3, cm -1 ): ν (C = O) = 1716 UV (methanol, nm): 253 (4.40, 307 (4.17)) Example 2
Kyselina benzo [ b ] fůro [ 3,2-b ] pyrol-2-karboxylová (1,5 g, 0,008 mol) sa přidá k acetanhydridu (20 ml). Zmes sa mieša pri 110°C po dobu 6 h. Reakčná zmes sa spracuje ako je uvedené v příklade 1.Benzo [b] furo [3,2-b] pyrrole-2-carboxylic acid (1.5 g, 0.008 mol) was added to acetic anhydride (20 mL). The mixture was stirred at 110 ° C for 6 h. The reaction mixture was worked up as outlined in Example 1.
Spektrálné meraniaSpectral measurements
Infračervené spektra sa namerali na spektrofotometr! SPECORD 71 IR (Caři Zeiss-Jena). Elektronové spektrá sa namerali na spektrofotometr UV VIS (Carl Zeiss-Jena) v oblasti 200 — 800 nm pri koncentráciach 2.10~5 mol. I-1. 4H NMR spektrá boli namerané na 80 MHz spektrofotometr BS 4887 C TESLA. Pri meraní sa použil vnútorný štandard tetrametylsilán. Chemické posuny á sa uvádzajú v ppm.Infrared spectra were recorded on a spectrophotometer! SPECORD 71 IR (Canis Zeiss-Jena). Electron spectra were recorded on a UV VIS spectrophotometer (Carl Zeiss-Jena) at 200-800 nm at concentrations of 2.10 -5 mol. I -1 . 1 H NMR spectra were recorded on a 80 MHz spectrophotometer BS 4887 C TESLA. The internal standard tetramethylsilane was used for the measurement. Chemical shifts sa are reported in ppm.
Zlúčenina podía vynálezu móže nájsť široké uplatnenie v syntéze nových heterocyklických zlúčenín, ako sú benzo (b)furo[3,2-b]azepíny, formylované benzo[b]furo[3,2b]pyroly a podobné.The compound of the invention may find wide application in the synthesis of novel heterocyclic compounds such as benzo (b) furo [3,2-b] azepines, formulated benzo [b] furo [3,2b] pyrrols and the like.
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS847850A CS240394B1 (en) | 1984-10-16 | 1984-10-16 | 1-acetylbenzo(b) furo (3,2-b) pyrrole and method of its preparation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS847850A CS240394B1 (en) | 1984-10-16 | 1984-10-16 | 1-acetylbenzo(b) furo (3,2-b) pyrrole and method of its preparation |
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| Publication Number | Publication Date |
|---|---|
| CS785084A1 CS785084A1 (en) | 1985-07-16 |
| CS240394B1 true CS240394B1 (en) | 1986-02-13 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS847850A CS240394B1 (en) | 1984-10-16 | 1984-10-16 | 1-acetylbenzo(b) furo (3,2-b) pyrrole and method of its preparation |
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| Country | Link |
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- 1984-10-16 CS CS847850A patent/CS240394B1/en unknown
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| Publication number | Publication date |
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| CS785084A1 (en) | 1985-07-16 |
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