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Synthesis 2007(10): 1503-1508  
DOI: 10.1055/s-2007-966025
PAPER
© Georg Thieme Verlag Stuttgart · New York

A New Approach to Pyrazino[2,1-b]quinazolines and Pyrazino[1,2-a]thi­eno[3,2-d]pyrimidines

Svetlana N. Kulika, Alexander S. Kobkob, Andrey A. Tolmacheva, Anton V. Tverdokhlebov*b, Oleg V. Shishkinc, Alexander N. Chernegad
a Kiev National Taras Shevchenko University, Volodimirska str. 62, 01033 Kiev, Ukraine
b Enamine Ltd., Alexandra Matrosova str. 23, 01103 Kiev, Ukraine
Fax: +380(44)5373253; e-Mail: atver@univ.kiev.ua;
c STC ‘Institute for Single Crystals’ NAS, 60 Lenina ave., 310001 Khar’kov, Ukraine
d Institute of Organic Chemistry NAS, Murmanska str. 5, 02094 Kiev, Ukraine
Further Information

Publication History

Received 13 February 2007
Publication Date:
02 May 2007 (online)

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Abstract

The reaction of [2-(chloromethyl)-4-oxo-3,4-dihydroquinazolin-3-yl]acetonitrile and 2-(chloromethyl)-3-(2-oxopropyl)quinazolin-4(3H)-one with aliphatic primary amines was shown to yield 2-alkyl-3-(alkylimino)-1,2,3,4-tetrahydro-6H-pyrazino[2,1-b]quinazolin-6-ones and 2-alkyl-3-methyl-1,2-dihydro-6H-pyrazino[2,1-b]quinazolin-6-ones, respectively. The starting­ materials were prepared by alkylation of 2-(chloromethyl)quinazolin-4(3H)-one with chloroacetonitrile or chloroacetone. Furthermore 2-alkyl-3-(alkylimino)-1,2,3,4,7,8,9,10-octahydro-6H-[1]benzothieno[2,3-d]pyrazino[1,2-a]pyrimidin-6-ones and 8-alkyl-2,3,7-trimethyl-8,9-dihydro-4H-pyrazino[1,2-a]thieno[2,3-d]pyrimidin-4-ones were obtained through the same sequence starting from the appropriate 2-(chloromethyl)thieno[2,3-d]pyrimidin-4(3H)-ones.

Key words

alkylations - heterocycles - nitriles - pyrazines - ring closure

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