Synthesis of 4‐Aminopyrimidines from 1,2,4‐Oxadiazoles, V1. Reductive Formation of 2‐(Benzoylamino)indole from 3‐(2‐Aminobenzyl)‐5‐phenyl‐1,2,4‐oxadiazole and Its Transformation to 6‐Phenyl‐8H‐pyrimido‐[1,6‐a: 4,5‐b']diindole, a New Heterocyclic Ring System

Imre Bata, Dezső Korbonits, P. Kolonits, Benjamin Podányi, Tünde Takácsy‐Erős, Kálmáan Simon

Research output: Article

7 Citations (Scopus)

Abstract

Catalytic hydrogenation of 5‐substituted 3‐(2‐aminobenzyl)‐1,2,4‐oxadiazoles 7 give 2‐(acylamino)indoles 10. Treatment of 2‐(benzoylamino)indoles 10a–c with acid leads to the novel 6‐phenyl‐8H‐pyrimido[1,6‐a: 4,5‐b']diindoles 19a–c. A route for the new ring formation is proposed. Catalytic hydrogenation of 19a (Raney nickel, 70°C, atmospheric pressure) saturates the 6‐phenyl ring but leaves the pentacyclic ring system intact. The structure of 19a is confirmed by an X‐ray crystallographic analysis.

Original languageEnglish
Pages (from-to)1835-1841
Number of pages7
JournalChemische Berichte
Volume126
Issue number8
DOIs
Publication statusPublished - 1993

ASJC Scopus subject areas

  • Chemistry(all)

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