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Synthesis of Carbolines via Microwave‐Assisted Cadogan Reactions of Aryl‐Nitropyridines
Author(s) -
Limbach Daniel,
Geffe Mario,
Detert Heiner
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702964
Subject(s) - aryl , microwave irradiation , chemistry , alkylation , ring (chemistry) , microwave , medicinal chemistry , transformation (genetics) , combinatorial chemistry , organic chemistry , catalysis , alkyl , biochemistry , gene , physics , quantum mechanics
Suzuki‐Miyaura‐couplings to aryl‐nitropyridines followed by Cadogan reactions is a straight‐forward method for the synthesis of δ‐ and β‐carbolines. Microwave irradiation of the nitrobiaryls in triethyl phosphite solutions conveniently gives moderate to very good yields of the carbolines. Reduction to the amines without cyclization occurs on certain substrates, and alkylation of the products is observed as a follow‐up reaction. Instead of α‐carbolines, naphthonitriles are generated by phosphite reduction and ring transformation.