A novel transformation of beta-1,2,3-thiadiazol-5-yl enamines into thieno{[}2,3-d]pyridazines / Rozin Yuri,Zhidovinov Sergey,Beryozkina Tetyana,Shafran Yuri,Lubec Gert,Eltsov Oleg,Slepukhin Pavel,Knippschild Uwe,Bischof Joachim,Dehaen Wim,Bakulev Vasiliy // TETRAHEDRON LETTERS. - 2015. - V. 56, l. 12. - P. 1545-1547.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

Reactions of beta-1,2,3-thiadiazol-5-yl enamines with acetyl chloride in 1,4-dioxane lead to the formation of either dienamines or novel thieno{[}2,3-d]pyridazines depending on the time and reaction temperature. Conditions were found for the selective synthesis of thieno{[}2,3-d]pyridazines. A plausible mechanism involves formation of C-S and C-C bonds and a novel ring rearrangement of 5-vinyl-1,2,3-thiadiazoles into pyridazine-4-thiolates. A series of new diamides of 2-(4-carboxy-1,2,3-thiadiazol-5-yl)thieno{[}2,3-d]pyridazine-7-carboxyli c acid is prepared by reaction of the methyl ester with primary and secondary amines. (C) 2015 Elsevier Ltd. All rights reserved.

Author keywords:

Enamines; Thieno{[}2,3-d]pyridazines; Thiadiazoles; Transformation; Rearrangement SELF-CONDENSATION; 1,2-DIAZA-1,3-BUTADIENES; CYCLOADDITION; DERIVATIVES; CHEMISTRY; RING

DOI:

10.1016/j.tetlet.2015.02.013

Web of Science ID:

ISI:000351247600019

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAR 18
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	SELF-CONDENSATION; 1,2-DIAZA-1,3-BUTADIENES; CYCLOADDITION; DERIVATIVES; CHEMISTRY; RING
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	tetber@mail.ru
Funding-Acknowledgement	RFBR {[}14-03-01033]; Ministry of Education and Science of the Russian Federation for Basic Research {[}4.1626.2014/K]
Funding-Text	This work was supported by RFBR (14-03-01033) and The Ministry of Education and Science of the Russian Federation for Basic Research (State task 4.1626.2014/K).
Number-of-Cited-References	30
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	27
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	CD7CE