Synthesis of Dihydro-3,1-benzoxazine Derivatives from 1,3-Amino Alcohols and N-Sulfonyl-1,2,3-triazole

An efficient rhodium-catalyzed synthesis of dihydro-3,1-benzoxazine derivatives has been accomplished from aniline derived 1,3-amino alcohols and N-sulfonyl-1,2,3-triazole. The developed reaction demonstrates the new reactivity of azavinyl carbenes and allows access to diverse substituted dihydro-3,1-benzoxazines in good yields. Importantly, the reaction was readily extended to diols and could be used for selective protection of amino alcohols with N-sulfonyl-1,2,3-triazole as the protecting reagent.

Automated summary

An efficient rhodium-catalyzed synthesis of dihydro-3,1-benzoxazine derivatives has been achieved from aniline derived 1,3-amino alcohols and N-sulfonyl-1,2,3-triazole. This reaction demonstrates the new reactivity of azavinyl carbenes and allows the synthesis of diverse substituted dihydro-3,1-benzoxazines in good yields. Furthermore, the reaction can be extended to diols and used for selective protection of amino alcohols using N-sulfonyl-1,2,3-triazole as the protecting reagent.