6-Polyfluoroalkylated 2-thiouracils in the synthesis of pyrimido{[}2,1-b]{[}1,3,5]thiadiazines by the double Mannich reaction / Khudina Ol'ga G.,Ivanova Anna E.,Burgart Yanina V.,Saloutin Victor I.,Kravchenko Marionella A. // JOURNAL OF FLUORINE CHEMISTRY. - 2013. - V. 147, l. . - P. 31-35.

ISSN/EISSN:

0022-1139 / 1873-3328

Type:

Article

Abstract:

6-Polyfluoroalkyl-2-thiouracils react with formaldehyde and primary amines in EtOH (MeCN) at 2-mercapto and 3-amino groups to yield pyrimido{[}2,1-b]{[}1,3,5]thiadiazines via the multicomponent double Mannich reaction. The structure of 3-benzyl-8-nonafluorobutyl-3,4-dihydro-2H,6H-pyrimido{[}2,1-b]{[}1,3,5]t hiadiazin-6-one was studied by the X-ray diffraction analysis. The use of ethylenediamine in these reactions yields 3,3'-ethane-1,2-diyl-bis(pyrimido{[}2,1-b]thiadiazinone) as a result of the bis-double Mannich cyclocondensation. 8-Polyfluoroalkyl-pyrimido{[}2,1-b]thiadiazines exhibit weak tuberculostatic activity. (C) 2013 Elsevier B.V. All rights reserved.

Author keywords:

The double Mannich reaction; 6-Polyfluoroalkyl-2-thiouracil; Formaldehyde; Aliphatic and aromatic amines; Ethylenediamine; Pyrimido{[}2,1-b]{[}1,3,5]thiadiazines; Tuberculostatic activity DERIVATIVES

DOI:

10.1016/j.jfluchem.2013.01.018

Web of Science ID:

ISI:000316710000006

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAR
Publisher	ELSEVIER SCIENCE SA
Address	PO BOX 564, 1001 LAUSANNE, SWITZERLAND
Language	English
EISSN	1873-3328
Keywords-Plus	DERIVATIVES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Inorganic \& Nuclear; Chemistry, Organic
Author-Email	kog@ios.uran.ru saloutin@ios.uran.ru
ResearcherID-Numbers	Burgart, Yanina/T-8025-2017
ORCID-Numbers	Burgart, Yanina/0000-0001-6061-2410
Funding-Acknowledgement	Ural Branch of the Russian Academy of Sciences {[}12-M-34-2064, 12-P-3-1035]; Russian Foundation for Basic Research {[}13-03-00617]; Council on Grants of the President of the Russian Federation {[}MK-837.2012.3]
Funding-Text	This work was supported by the Ural Branch of the Russian Academy of Sciences (Grant No. 12-M-34-2064, 12-P-3-1035), the Russian Foundation for Basic Research (Grant No. 13-03-00617) and the Council on Grants of the President of the Russian Federation (Grant No. MK-837.2012.3).
Number-of-Cited-References	14
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	10
Journal-ISO	J. Fluor. Chem.
Doc-Delivery-Number	113ZU