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Reaction of N,N'-Dimethyl-2-nitroethene-1,1-diamine with alpha,beta-Unsaturated Acyl Isothiocyanates: Preparation of 1,3-Thiazin-4-one and 4-Nitro-1,2-thiazol-5(2H)-imine Derivatives


Garcia Trimino, Maria I; Macias Cabrera, Arturo; Velez Castro, Herman; Rosado Perez, Aristide; Moya Argilagos, Dally; Linden, Anthony; Heimgartner, Heinz (1998). Reaction of N,N'-Dimethyl-2-nitroethene-1,1-diamine with alpha,beta-Unsaturated Acyl Isothiocyanates: Preparation of 1,3-Thiazin-4-one and 4-Nitro-1,2-thiazol-5(2H)-imine Derivatives. Helvetica Chimica Acta, 81(3-4):718-728.

Abstract

The reaction of N,N-dimethyl-2-nitroethene-1,1-diamine (8) with alpha,beta-unsaturated acyl isothiocyanates 9 affords 3,3-diamino-2-nitroacrylthioamides 10 (Scheme 2) in moderate-to-good yields. Cyclization of 10 under acidic conditions gives 1,3-thiazin-4-one derivatives of type 11. Oxidative cyclization of 10 with diethyl azodicarboxylate leads to 4-nitro-1,2-thiazol-5(2H)-imlne derivatives 12.

Abstract

The reaction of N,N-dimethyl-2-nitroethene-1,1-diamine (8) with alpha,beta-unsaturated acyl isothiocyanates 9 affords 3,3-diamino-2-nitroacrylthioamides 10 (Scheme 2) in moderate-to-good yields. Cyclization of 10 under acidic conditions gives 1,3-thiazin-4-one derivatives of type 11. Oxidative cyclization of 10 with diethyl azodicarboxylate leads to 4-nitro-1,2-thiazol-5(2H)-imlne derivatives 12.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1998
Deposited On:12 Nov 2013 14:14
Last Modified:05 Apr 2016 17:07
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Swiss Federal Government, National Scholarship for Foreign Students
Publisher DOI:https://doi.org/10.1002/hlca.19980810321

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