CS240394B1 - 1-Acetylbenzo[bjfuro(3^2-bJpyrol a sposob jeho přípravy - Google Patents
1-Acetylbenzo[bjfuro(3^2-bJpyrol a sposob jeho přípravy Download PDFInfo
- Publication number
- 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
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- furo
- pyrrole
- acetylbenzo
- preparation
- benzo
- Prior art date
Links
- 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
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
240394
Vynález sa týká l-acetylbenzo[h]furo-[3,2-b] pyrolu a spósobu jeho přípravy.Vhodnou metodou na jeho přípravu, je de-karboxylačná acetylácia kyseliny benzo[b]-furo[3,2-b]pyrol-2-karboxylovej. Všeobecne dekarboxylácia karboxylovýchkyselin představuje jednoduchá reakclú,ktorú možno uskutočnit viacerými postup-mi. Výběr metódy ovplyvňuje najma štruk-túra východiskovej kyseliny, jej fyzikálno--chemické vlastnosti, ako aj fyzikálně a che-mické vlastnosti očakávaného produktu.Váčšina dekarboxylačných reakcií sa rea-lizuje v kvapalnej fáze bez katalyzátore,alebo v přítomnosti homogenného či tuhé-ho katalyzátora.
Dusíkové heterocyklické zlúčeniny s NHvazbou napr. pyrol, indol alebo karbazolsa alkylujú alebo acylujú vo formě aniónugenerovaného ich reakciou so silnou zása-dou, ako je napr. amid sodný, hydrid litnýalebo organokovy. V literatuře sú opísanéalkylácie 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-eto-xykarbonyl-furo[3,2-b]pyrolu cestou N-lít-nej soli sme popísali v náročných reakč-ných podmienkach [Krutošíková A., KováčJ., Chudobová M., Ilavský D., Collection Cze-choslov. Chem. Commun. 45, 2 949 (1980)].
Studium literatúry ukázalo, že 1-acetyl-benzo[b]fůro[3,2-b]pyrol nebol doteraz při-pravený.
Predmetom vynálezu je 1-acetylbenzo-[b]furo[3,2-b]pyrol vzorca I
a spósob jeho přípravy.
Podstata spósobu přípravy 1-acetylbenžo-
[b]furo[3,2-b] pyrolu vzorca I spočívá vtom, že sa kyselina benzo[b]furo[3,2-b]py-rol-2-karboxylová vzorca II
(IH zahrieva v acetanhydride pri teplotách 110až 136 °C. Výhody spósobu přípravy zlúčeniny I po-dlá vynálezu spočívajú okrem iného v tom,že sa reakcia dekarboxylácie a súčasnejacetylácie uskutočňuje v jednom stupni vnenáročných podmienkach s dobrým výťaž-kom, pričom sa získá stabilizovaný 1-acé-tylbenzo [ b ] fůro (3,2-b ] pyrol.
Predmet vynálezu ilustrujú, ale neobmed-zujú následovně příklady: Přikladl
Kyselina benzo [ b ] fůro [ 3,2-b ] pyr ol-2-kar-boxylová (1,5 g, 0,0008 mol) a acetanhyd-rid (20 ml) se refluxuje za miešania 4 h.Reakčná zmes sa za horúca přefiltruje, roz-tok sa zahustí a po ochladení vylúčený su-rový produkt I sa odsaje a prekryštalizuje.Výťažok 1 g (66 %), t. t. 101 °C (etanol).Pre C12H9NO2 (199,2) vypočítané7,03 % N, nájdené7,30 % N. Štrpktúra zlúčeniny I bola dokázaná spek-trálnými metodami: IR, UV, XH NMR. IR (CHCI3, cm’1): v (C=O) = 1716UV (metanol, nm): 253 (4,40, 307 (4,17) Příklad 2
Kyselina benzo [ b ] fůro [ 3,2-b ] pyrol-2-kar-boxylová (1,5 g, 0,008 mol) sa přidá k acet-anhydridu (20 ml). Zmes sa mieša pri 110°Cpo dobu 6 h. Reakčná zmes sa spracuje akoje uvedené v příklade 1.
Spektrálné merania
Infračervené spektrá sa namerali na spek-trofotometri SPECORD 71 IR (Carl Zeiss--Jena). Elektronové spektrá sa namerali naspektrofotometri UV VIS (Carl Zeiss-Jena)v oblasti 200 — 800 nm pri koncentráciach2.10~5 mol. 1_1. Ή NMR spektrá boli na-merané na 80 MHz spektrofotometri BS4887 C TESLA. Pri meraní sa použil vnútor-ný standard tetrametylsilán. Chemické po-suny á sa uvádzajú v ppm.
Zlúčenina podlá vynálezu móže nájsť ši-roké uplatnenie v syntéze nových hetero-cyklických zlúčenín, ako sú benzo [b]furo-[3,2-b]azepíny, formylované benzo[b]furo-[3,2b]pyroly a podobné.
Claims (2)
- 240394 VYNÁLEZU 1. l-Acetylbenzo[b]furo[3,2-b]pyrol vzor-ca I
- 2. Spósob prípi’avy l-acetylbenzo[b]furo-[3,2-b]pyrolu podl'a bodu 1 vyznačený tým, že sa kyselina benzo[b]furo[3,2-b]pyrol-2--karboxylová vzorca IIzahrieva v acetanhydride pri teplotách 110až 136°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS847850A CS240394B1 (cs) | 1984-10-16 | 1984-10-16 | 1-Acetylbenzo[bjfuro(3^2-bJpyrol a sposob jeho přípravy |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS847850A CS240394B1 (cs) | 1984-10-16 | 1984-10-16 | 1-Acetylbenzo[bjfuro(3^2-bJpyrol a sposob jeho přípravy |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS785084A1 CS785084A1 (en) | 1985-07-16 |
| CS240394B1 true CS240394B1 (cs) | 1986-02-13 |
Family
ID=5428382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS847850A CS240394B1 (cs) | 1984-10-16 | 1984-10-16 | 1-Acetylbenzo[bjfuro(3^2-bJpyrol a sposob jeho přípravy |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS240394B1 (cs) |
-
1984
- 1984-10-16 CS CS847850A patent/CS240394B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS785084A1 (en) | 1985-07-16 |
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