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A Unified Approach to the Isomeric α-, β-, γ-, and δ-Carbolines via their 6,7,8,9-Tetrahydro Counterparts
Author(s) -
Qiao Yan,
Emma Gin,
Martin G. Banwell,
Anthony C. Willis,
Paul D. Carr
Publication year - 2017
Publication title -
the journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.7b00323
Subject(s) - chemistry , combinatorial chemistry , coupling (piping) , palladium , coupling reaction , computational chemistry , catalysis , organic chemistry , mechanical engineering , engineering
A cross-coupling/reductive cyclization protocol has been employed in a unified approach to all four carbolines. So, for example, the 2-nitropyridine 8, which is readily prepared through an efficient palladium-catalyzed Ullmann cross-coupling reaction, is reductively cyclized under conventional conditions to give 6,7,8,9-tetrahydro-α-carboline that is itself readily aromatized to give α-carboline (1).

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