Simple method for preparation of Dialkyl (2,3-dihydro-1,3-thiazol-2-yl)-phosphonates - Publication - Bridge of Knowledge

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Simple method for preparation of Dialkyl (2,3-dihydro-1,3-thiazol-2-yl)-phosphonates

Abstract

Abstract A simple synthesis of dialkyl (2,3-dihydro-1,3-thiazol-2-yl)-phosphonates from thiazoliumsalts and trialkyl phosphites is described. The series of dialkyl (2,3-dihydro-1,3-thiazol-2-yl)-phosphonates with various substituents in positions 3, 4, and 5 of the thiazole ring wereprepared. However, only phosphonates with an aryl on the nitrogen atom were stable enoughfor chromatographic purification, although all the new phosphonates are very sensitive tooxidation. We made efforts to apply dialkyl (2,3-dihydro-1,3-thiazol-2-yl)-phosphonates in aHorner-Wadsworth-Emmons reaction, but the generated antiaromatic anion of phosphonatedecomposed quickly, even at −70◦C.

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Category:
Articles
Type:
artykuł w czasopiśmie wyróżnionym w JCR
Published in:
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS no. 186, pages 12 - 20,
ISSN: 1042-6507
Language:
English
Publication year:
2010
Bibliographic description:
Janikowska K., Makowiec S.: Simple method for preparation of Dialkyl (2,3-dihydro-1,3-thiazol-2-yl)-phosphonates// PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS. -Vol. 186, nr. iss. 1 (2010), s.12-20
Verified by:
Gdańsk University of Technology

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