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First synthesis of novel pentaheterocyclic ring system of 1,2,4-triazolo[2″,3″:6′,1′]pyrimido[4′,5′:2,3]pyrido[1,2-a]benzimidazole

✍ Scribed by Nehal M. Elwan


Publisher
Journal of Heterocyclic Chemistry
Year
2004
Tongue
English
Weight
124 KB
Volume
41
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

Reaction of 1‐amino‐3‐arylpyrido[1,2‐a]benzimidazole‐2,4‐dicarbonitrile (1) with dimethylformamide‐dimethylacetal (DMF‐DMA) gave 1‐[N,N‐(dimethylaminomethylene)amino]‐3‐arylpyrido[1,2‐a]benzimidazole‐2,4‐dicarbonitrile (2). Compounds (1) reacted with triethylorthoformate yielding 1‐[N‐(ethoxymethylene)amino]‐3‐arylpyrido[1,2‐a]benzimidazole‐2,4‐dicarbonitrile (3). 3‐Amino‐4‐imino‐5‐aryl‐6‐cyanopyrimido[5′,4′:5,6]pyrido[1,2‐α] benzimidazole (4) was synthesized via condensation of either (2) or (3) with hydrazine hydrate. Reactions of (4) with acetic anhydride, ethyl chloroformate or aryl isothiocyanate yielded the respective derivative of the new ring system namely 1,2,4‐triazolo[2″,3″:6′,1′]pyrimido[4′,5′:2,3]pyrido[1,2‐a]benzimidazole (5–7).


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## Abstract magnified image 4‐Acetyl‐5‐methyl‐1‐phenyl‐1__H__‐pyrazole reacts with dimethylformamide dimethylacetal (DMF‐DMA) to afford the corresponding (__E__)1‐(5‐methyl‐1‐phenyl‐1__H__‐pyrazol‐4‐yl)‐3‐(__N,N__‐dimethylamino)‐2‐propen‐1‐one. The latter product undergoes regioselective 1,3‐dipol