AZA-ENAMINES .8. ELECTROPHILIC SUBSTITUTION-REACTIONS AT THE AZOMETHINE C-ATOM OF ALDEHYDE DIALKYLHYDRAZONES - VILSMEIER FORMYLATION AND CONSECUTIVE REACTIONS

被引：32

作者：

BREHME, R

机构：

[1] Berlin-Chemie Ag, Abteilung Chemische Forschung, Berlin, DDR‐1199

来源：

CHEMISCHE BERICHTE | 1990年 / 123卷 / 10期

关键词：

Aza‐enamines; Hydrazones; Phenylglyoxal monohydrazones; Pyrrolo[1,2‐b][1,2,4]triazinium salts; Pyrrolo[2,1‐b]imidazoles; Triazapentadienium salts;

D O I：

10.1002/cber.19901231015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Aza‐enamines, VIII. — Electrophilic Substitution Reactions at the Azomethine C‐Atom of Aldehyde Dialkylhydrazones: Vilsmeier Formylation and Consecutive Reactions The reaction of hydrazones 1 with the Vilsmeier reagent yields 3‐phenyl‐1,4,5‐triaza‐1,3‐pentadienium salts according to their aza‐enamine character. Hydrolysis of 2 gives 1‐phenylglyoxal 1‐dialkylhydrazones 3, which rearrange in acidic media to 1‐phenylglyoxal 2‐dialkylhydrazones 4. Compound 3h forms the dihydropyrroloimidazole 5 in boiling ethanol. Pyrrolotriazinium salt 6 is obtained by the reaction of 1b with the isolated Vilsmeier reagent from dimethylformamide/oxalyl chloride. Copyright © 1990 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

引用

页码：2039 / 2046

页数：8

共 24 条

[1] AZO ANIONS IN SYNTHESIS - TERT-BUTYLHYDRAZONES AS ACYL-ANION EQUIVALENTS [J].