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Aza‐Henry Reactions of 3,4‐Dihydroisoquinoline
Author(s) -
Ahamed Muneer,
Thirukkumaran Thiru,
Leung Wing Yan,
Jensen Paul,
Schroers Jade,
Todd Matthew H.
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.201000955
Subject(s) - chemistry , nitromethane , tautomer , vicinal , nitroaldol reaction , alkylation , coupling reaction , acylation , lewis acids and bases , nucleophile , leaving group , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , enantioselective synthesis
The aza‐Henry reaction of 3,4‐dihydroisoquinoline is reported. The reaction is favourable in excess nitromethane under ambient conditions. Isolation of the unstable reaction product is achieved by acylation or alkylation, allowing the synthesis of Reissert‐like compounds in good yields from a one‐pot, three‐component coupling. The rates of reaction for dihydroisoquinoline and the corresponding benzylisoquinolinium ion have been investigated in the presence and absence of base. The reaction with dihydroisoquinoline probably proceeds via an azinic acid tautomer of nitromethane, a reaction pathway unavailable to the isoquinolinium ion. The traditionally problematic reduction of two of the resulting β‐nitroamine derivatives was achieved, providing access to a number of new chiral vicinal diamines.