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Efficient and Practical One‐Pot Conversions of N ‐Tosyltetrahydroisoquinolines into Isoquinolines and of N ‐Tosyltetrahydro‐β‐carbolines into β‐Carbolines through Tandem β‐Elimination and Aromatization
Author(s) -
Dong Jing,
Shi XiaoXin,
Yan JingJing,
Xing Jing,
Zhang Qiang,
Xiao Sen
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001153
Subject(s) - aromatization , chemistry , tosyl , tandem , dimethyl sulfoxide , sulfoxide , base (topology) , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , mathematical analysis , materials science , mathematics , composite material
An efficient, practical, and general method for conversions of N ‐tosyltetrahydroisoquinolines ( N ‐tosyl‐THIQs) into isoquinolines and of N ‐tosyltetrahydro‐β‐carbolines ( N ‐tosyl‐THBCs) into β‐carbolines is described. Treatment of N ‐tosyl‐THIQs or N ‐tosyl‐THBCs with base in dimethyl sulfoxide afforded dihydroisoquinolines or dihydro‐β‐carbolines as intermediates, and these were then oxidized in situ by molecular oxygen to furnish isoquinolines or β‐carbolines in good to high yields. Both one‐pot conversions occurred through tandem β‐elimination and aromatization.