Synthesis of Novel 2-Oxo-1,2,4-[triazolo][3,2-d] [1,5]benzoxazepine Derivatives

Abstract

Abstract: Many [1,2,4]triazolobenzoheteroazepine derivatives show interesting biological activities. In this paper, the geminal arylazo isocyanato compounds 3 were prepared from chroman-4-ones in three steps, i.e. condensation with arylhydrazine, cycloaddition of the resulting hydrazone with HNCO, and oxidative ring cleavage by KMnO₄. Compounds 3 were allowed to react with HBF₄, producing the respective 3-spiro substituted 1-aryl-4,5-dihydro-5-oxo-3H-1,2,4-triazolium salts 4. The concurrent rearrangement of compound 4 with insertion of the nitrogen atom into the carbon skeleton provided, after the basic work-up, 2-oxo-[1,2,4]triazolo[3,2-d][1,5]benzoxazepines 5a—5h. An unambigous structutal proof was obtained from the X-ray diffraction analysis for compound 5h.

Key words: Geminal arylazo isocyanates, Ring closure, Rearrangement, 2-Oxo-[1,2,4]triazolo[3,2-d][1,5]benzoxazepines

CLC Number:

O626

TrendMD:

LI Zheng, WANG Quan-Rui, TAO Feng-Gang . Synthesis of Novel 2-Oxo-1,2,4-[triazolo][3,2-d] [1,5]benzoxazepine Derivatives[J]. Chem. J. Chinese Universities, 2004, 25(10): 1840.

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Synthesis of Novel 2-Oxo-1,2,4-[triazolo][3,2-d] [1,5]benzoxazepine Derivatives

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