Tetrahedron p. 13841 - 13854 (1997)
Update date:2022-08-02
Topics:
Sharma, Arun K.
Mahajan, Mohinder P.
4-(N-Allyl-N-aryl)amino-1,3-diaza-1,3-butadienes 2, prepared by the treatment of N-arylamino-1,3-diaza-1,3-butadienes 1 with allyl bromide, underwent [4+2] cycloadditions with vinyl/isopropenyl- and accompanied by rearrangements in case of chloroketenes, to yield 5-vinyl/isopropenyl pyrimidinones 5 and 5-methylthio pyrimidinones 19, respectively. The pyrimidinones 5 on refluxing in xylene gave pyrimidoazepines 6, underwent annelation reaction, in refluxing benzene in presence of AlCl3, to yield pyrimidoquinolines 7 and on treatment with DMAD in refluxing toluene, underwent [4+2] cycloaddition accompanied by the elimination of N-allylarylamine functionality to yield quinazolinone 9. Further, the reactions of 5 with PhSH in the presence of AIBN in refluxing benzene followed unusual radical cyclisation involving N-aryl group leading to pyrimidoquinolines 10. The iodocyclisation of pyrimidinones 19 yielded pyrimidothiazines 20.
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Doi:10.1016/0045-2068(78)90013-5
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