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Regiospecific bromination of (2е, 4е) -5-aryl-2- (4-arylthiazol-2-yl) penta-2,4-dienenitriles
*
1
,
S. G. Krivokolysko
*
1
,
*
2
,
K. A. Frolov
*
1
Academic Editor: György Keglevich
Published:
14 November 2021
by MDPI
in The 25th International Electronic Conference on Synthetic Organic Chemistry
session General Organic Synthesis
https://doi.org/10.3390/ecsoc-25-11783
(registering DOI)
Abstract:
In the reaction of (2E, 4E) -5-phenyl-2-cyano-2,4-pentadientioamide or (E) -3- (2-nitrophenyl) acrolein and cyanothioacetamide with α-bromoketones received new (2E, 4E) -5-aryl-2- (4-arylthiazol-2-yl) penta-2,4-dienenitriles. Direct bromination of the latter by the action of Br2 in DMF proceeds regiospecifically at the C5 position of the thiazole ring without affecting the diene system and leads to the formation of previously undescribed (2E, 4E) -5-aryl-2- (5-bromo-4-arylthiazol-2-yl) penta-2,4-diennitriles. The structure of the reaction products was established using 2D NMR spectroscopy and X-ray diffraction analysis.
Keywords: 1,3-thiazoles, 5-bromo-1,3-thiazoles, cyanothioacetamide, 2-cyanothioacrylamides, bromination
