2-Methylsulfanyl-6-Polyfluoroalkyl-Pyrimidin-4-Ones: Synthesis and Nucleophilic Substitution Reactions / Khudina O. G.,Burgart Ya. V.,Saloutin V. I. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2014. - V. 50, l. 6. - P. 856-863.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

We have optimized the reaction conditions for the synthesis of 2-methylsulfanyl-6-polyfluoro-alkylpyrimidin-4-ones. In particular the yield of trifluoromethyl-substituted heterocycle was increased to 96\%, and new polyfluoroalkyl-substituted analogs were prepared. The interaction of these heterocycles with morpholine or hydrazine was shown to result in nucleophilic substitution of the methylsulfanyl group, leading to 2-morpholino- and 2-hydrazino-6-polyfluoroalkylpyrimidin-4-ones. The reaction of 2-(2-phenylhydrazino)-6-trifluoromethylpyrimidin-4-one with paraform produced 5-oxo-2-phenyl-7-tri-fluoromethyl-5H-1,2,4-triazolo{[}4,3-D degrees]pyrimidin-1-id-2-ium. The lactam structure of the synthesized heterocycles was established by X-ray structural analysis, as well as by IR and NMR spectroscopy.

Author keywords:

hydrazines; 2-methylsulfanyl-6-polyfluoroalkylpyrimidin-4-one; morpholine; nucleophilic substitution; X-ray structural analysis DERIVATIVES; PYRIMIDINES; ANALOGS

DOI:

10.1007/s10593-014-1539-7

Web of Science ID:

ISI:000340878300007

Соавторы в МНС:

Другие поля

Поле	Значение
Month	SEP
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	DERIVATIVES; PYRIMIDINES; ANALOGS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	burgart@ios.uran.ru
ResearcherID-Numbers	Burgart, Yanina/T-8025-2017
ORCID-Numbers	Burgart, Yanina/0000-0001-6061-2410
Funding-Acknowledgement	Russian Foundation for Basic Research {[}13-03-00617]; Grants Council of the President of the Russian Federation {[}NSh-3656.2014.3]
Funding-Text	The work was performed with financial support from the Russian Foundation for Basic Research (grant 13-03-00617) and the Grants Council of the President of the Russian Federation (grant NSh-3656.2014.3).
Number-of-Cited-References	29
Usage-Count-Since-2013	4
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	AN8TV