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
ADLINGTON, RM
BALDWIN, JE
BOTTARO, JC
PERRY, MWD
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (18) : 1040 - 1041
[2] AZAENAMINES .3. ELECTROPHILIC SUBSTITUTION-REACTIONS ON CARBON-ATOM OF AZOMETHINE GROUP IN ALDEHYDE-N,N-TETRAMETHYLENE HYDRAZONES
BREHME, R
NIKOLAJEWSKI, HE
[J]. TETRAHEDRON, 1976, 32 (06) : 731 - 736
[3] AZA - ENAMINES .7. UMPOLUNG OF THE AZOMETHINE REACTIVITY IN THE REACTION OF ALDEHYDE HYDRAZONES WITH SULFONYL ISOCYANATES SUBSTITUENT EFFECTS
BREHME, R
KLEMANN, A
[J]. TETRAHEDRON, 1987, 43 (18) : 4113 - 4118
[4] AZA-ENAMINES .6. REACTIONS OF N,N-DIALKYLHYDRAZONES OF AROMATIC-ALDEHYDES WITH SULFONYL ISOCYANATES
BREHME, R
STROEDE, B
[J]. JOURNAL FUR PRAKTISCHE CHEMIE, 1987, 329 (02): : 246 - 258
[5] BREHME R, 1968, Z CHEM, V8, P226
[6] BREHME R, 1985, SCHRIFT PROMOTION B
[7] BREHME R, IN PRESS J PRAKT CHE
[8] BREHME R, 1982, TETRAHEDRON LETT, P1131
[9] AZA-ENAMINES .4. PROOF OF ENAMINE CHARACTER OF N,N-ALKYLATED HYDRAZONES GIVEN BY NMR-SPECTROSCOPY AND UV-SPECTROSCOPY
GRUNDEMANN, E
BREHME, R
NIKOLAJEWSKI, HE
[J]. JOURNAL FUR PRAKTISCHE CHEMIE, 1982, 324 (04): : 575 - 580
[10] ELECTROPHILIC SUBSTITUTION-REACTION AT AZOMETHINE CARBON-ATOM - ACYLATION OF ALIPHATIC ALDEHYDE HYDRAZONES
KAMITORI, Y
HOJO, M
MSUDA, R
YOSHIDA, T
OHARA, S
YAMADA, K
YOSHIKAWA, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) : 519 - 526

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