A new one-pot preparation of 4-tetrazolyl-3,4-dihydroquinazolines
has been reported. The Ugi-azide reactions of 2-azidobenzaldehydes,
amines, trimethylsilyl azide, and isocyanides produced azide intermediates
without separation, which were treated with isocyanides to give 4-tetrazolyl-3,4-dihydroquinazoline
derivatives through a sequential Palladium-catalyzed azide-isocyanide
cross-coupling/cyclization reaction in moderate to good yields. The
biological evaluation demonstrated that compound 6c inhibited
breast cancer cells well and displayed broad applications for synthesis
and medicinal chemistry.
A new, one-pot method for the synthesis of 4H-3,1-benzoxazine derivatives has been developed. The Passerini-azide reactions of 2-azidobenzaldehydes, trimethylsilyl azide, and isocyanides produced azide intermediate without separation, which then reacted with isocyanides to give 4H-3,1-benzoxazine derivatives via a tandem one-pot palladium-catalyzed azide–isocyanide coupling/cyclization reaction in moderate to good yields.
A new one-pot preparation of polysubstituted imidazoles by a Staudinger/aza-Wittig/Ag(I)-catalyzed cyclization/isomerization has been developed. The easily accessible propargylazide derivatives reacted with triphenylphosphine, isocyanates, and amines sequentially to produce the fully substituted imidazoles in good overall yields in the presence of catalytic amount of AgNO/DMAP.
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