A simple synthesis of dimethyl 2-[(Z)-3-amino-1-oxo-1-(substituted)but-2-en-2-yl]fumarates: potential intermediates in the synthesis of polysubstituted five- and six-membered heterocycles-Reference-Cited by-同舟云学术

A simple synthesis of dimethyl 2-[(Z)-3-amino-1-oxo-1-(substituted)but-2-en-2-yl]fumarates: potential intermediates in the synthesis of polysubstituted five- and six-membered heterocycles

Published:2016-04-12 Issue:6 Volume:71 Page:677-682
ISSN:1865-7117
Container-title:Zeitschrift für Naturforschung B
language:en
Short-container-title:

Author:

Šinkovec Rok¹,Grošelj Uroš¹,Prek Benjamin¹,Počkaj Marta¹,Ričko Sebastijan¹,Svete Jurij¹,Stanovnik Branko¹

Affiliation:

1. Faculty of Chemistry and Chemical Technology, University of Ljubljana , P.O. Box 537, Večna pot 113, 1000 Ljubljana, Slovenia

Abstract

Abstract In this communication, a simple synthesis of dimethyl 2-[(Z)-3-amino-1-oxo-1-(substituted)but-2-en-2-yl]fumarates is described. Methyl ketones were transformed by treatment with N,N-dimethylacetamide dimethyl acetal (DMADMA) into 3-dimethylamino-1-(substituted)but-2-en-1-ones, followed by treatment with ammonium acetate into (Z)-3-amino-1-(substituted)but-2-en-1-ones and addition to dimethyl acetylenedicarboxylate. These novel polysubstituted butadienes are potential intermediates for the metal-free preparation of polysubstituted five- and six-membered heterocycles.

Publisher

Walter de Gruyter GmbH

Subject

General Chemistry

Link

https://www.degruyter.com/document/doi/10.1515/znb-2016-0017/pdf

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