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

Autor: Rupa K; Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India., Yadagiri D; Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India., Bagavathi R; Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India., Anbarasan P; Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2023 May 19; Vol. 25 (19), pp. 3375-3379. Date of Electronic Publication: 2023 May 08.
DOI: 10.1021/acs.orglett.3c00851
Abstrakt: 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.
Databáze: MEDLINE