The surprising nucleophilic addition of aminochlorocarbenes to diethyl acetylenedicarboxylate and to oxalyl chloride: quinolines and benzo[1,4]diazepines from N-alkylformanilides and oxalyl chloride in the presence of Hünig's base

Ying Cheng; Hua Yang; Otto Meth-Cohn

doi:10.1039/B307278A

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The surprising nucleophilic addition of aminochlorocarbenes to diethyl acetylenedicarboxylate and to oxalyl chloride: quinolines and benzo[1,4]diazepines from N-alkylformanilides and oxalyl chloride in the presence of Hünig's base

Ying Cheng,*^a Hua Yang^a and Otto Meth-Cohn*^b

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* Corresponding authors

^a Department of Chemistry, Beijing Normal University, Beijing 100875, China
E-mail: yincheng@95777.com
Tel: +86 1062205558

^b Chemistry Department, Sunderland University, Sunderland, UK
E-mail: otto.meth-cohn@sunderland.ac.uk

Abstract

Vilsmeier reagents derived from N-methylformanilides undergo ready deprotonation with Hünig's base. In xylene, the derived nucleophilic arylaminochlorocarbenes bearing 4-methyl- and 4-methoxy-substituents react with acetylenedicarboxylates to give 2-(2-chloro-1,2-bis(ethoxycarbonyl)vinyl)-3,4-bis(ethoxycarbonyl)-1-methyl-1,2-dihydroquinolines while most derivatives react with oxalyl chloride to give substituted 1-methyl-4-phenylbenzo[f][1,4]diazepine-2,3-dicarboxylic anhydrides.

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Article information

DOI: https://doi.org/10.1039/B307278A
Article type: Paper
Submitted: 27 Jun 2003
Accepted: 01 Sep 2003
First published: 17 Sep 2003

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Org. Biomol. Chem., 2003,1, 3605-3610

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The surprising nucleophilic addition of aminochlorocarbenes to diethyl acetylenedicarboxylate and to oxalyl chloride: quinolines and benzo[1,4]diazepines from N-alkylformanilides and oxalyl chloride in the presence of Hünig's base

Y. Cheng, H. Yang and O. Meth-Cohn, Org. Biomol. Chem., 2003, 1, 3605 DOI: 10.1039/B307278A

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Organic & Biomolecular Chemistry

The surprising nucleophilic addition of aminochlorocarbenes to diethyl acetylenedicarboxylate and to oxalyl chloride: quinolines and benzo[1,4]diazepines from N-alkylformanilides and oxalyl chloride in the presence of Hünig's base

Abstract

Supplementary files

Article information

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The surprising nucleophilic addition of aminochlorocarbenes to diethyl acetylenedicarboxylate and to oxalyl chloride: quinolines and benzo[1,4]diazepines from N-alkylformanilides and oxalyl chloride in the presence of Hünig's base

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