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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