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A new efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4 H -3,1-benzothiazines via sequential Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reaction has been developed. The three-component Passerini reactions of 2-azidobenzaldehydes  1 , benzoic acid ( 2 ), and isocyanides  3  produced the azide intermediates  4 , which were treated sequentially with triphenylphosphine, isocyanates (or CS 2 ), and secondary amines to give polysubstituted 3,4-dihydroquinazolines  8  and 4 H -3,1-benzothiazines  11  in good overall yields through consecutive Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reactions.

beilstein journal of organic chemistry

New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4<i>H</i>-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence

New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence