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

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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