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HETEROCYCLES FROM NITRILE OXIDES: SYNTHESIS AND REACTIONS OF 2-THIENOYLHYDROXAMOYL CHLORIDE

1988; Taylor & Francis; Volume: 40; Issue: 1-2 Linguagem: Inglês

10.1080/03086648808072891

0308-664X

Abdou O. Abdelhamid, Fathy A. Khalifa, Sami S. Ghabrial,

Quinazolinone synthesis and applications

Abstract Nitroso derivatives of imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine and imidazo[1,2-a]pyrazine were obtained in good yields by the action of 2-thienoylhydroxamoyl chloride (2) on 2-aminopyridines, 2-aminopyrimidine and 2-aminopyrazine, respectively. Benzotriazine, benzothiadiazine and quinazoline were obtained from 2 via its reactions with o-phenylendiamine, o-aminothiophenol and methylanthranilate, respectively. 2 was treated with ethylenic and acetylenic dipoloraphiles to afford 3-thienoylisoxazolines and isoxazole, respectively. The structures of the products were assigned and confirmed on the basis of their elemental analyses, spectral data and alternative synthesis wherever possible.