Synthesis of Pyridoisoindoles through Diazotization Followed by Intramolecular Cyclization from Pyridinylarylacetates in One Pot

• Published in: Advanced synthesis & catalysis Vol. 357; no. 13; pp. 2903 - 2912
• Main Authors: Kim, Cheol-Eui, Baek, Yonghyeon, Kim, Sung Hong, Lee, Phil Ho
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 14.09.2015; WILEY‐VCH Verlag; Wiley
• Subjects: carbenes; Catalysis; Catalysts; Chemistry; Chemistry, Applied; Chemistry, Organic; copper; metal-free conditions; Physical Sciences; pyridinylarylacetates; pyridoisoindoles; Science & Technology; Synthesis; pyridinylarylacetates; carbenes; CATALYZED REACTION; TERMINAL ALKYNES; TRANSANNULATION; REARRANGEMENT; CYCLOADDITION; metal-free conditions; N-SULFONYL AZIDES; FACILE SYNTHESIS; 2-ARYLPYRIDINES; copper; DIHYDROPYRROLES; DERIVATIVES; pyridoisoindoles
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201500433

A robust synthetic method for a variety of pyridoisoindoles from pyridinylarylacetates has been developed through diazotization using 4‐methylbenzenesulfonyl azide and 1,8‐diazabicyclo[5.4.0]undec‐7‐ene followed by intramolecular cyclization via elimination of a nitrogen molecule under copper(II) trifluoromethanesulfonate‐catalyzed conditions in a one‐pot process. The intramolecular cyclization also took place efficiently with diazo substrates to produce pyridoisoindoles in good to excellent yields under metal‐free conditions or catalytic conditions [1.0 mol% copper(II) trifluoromethanesulfonate, 25 °C].