Premium
Mannich and eschweiler‐clarke reaction of 1‐benzyl‐1,2,3,4‐tetrahydroisoquinolines. Studies on the syntheses of heterocyclic compounds. Part CCCXVIII
Author(s) -
Kametani T.,
Noguchi I.,
Saito K.
Publication year - 1969
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570060616
Subject(s) - chemistry , mannich reaction , yield (engineering) , iif , organic chemistry , mannich base , medicinal chemistry , catalysis , materials science , biology , antibody , immunology , metallurgy , autoantibody
Modified Mannich reactions of a number of 1‐benzyl‐1,2,3,4‐tetrahydroisoquinolines (Ia‐Ie) were attempted to afford the corresponding protoberberine derivatives (IIa‐IIe) in good yield. Treatment of both If and Ig with formalin under a variety of Mannich or Eschweiler‐Clarke conditions did not give the expected protoberberine derivatives IIf and IIg, but afforded the N ‐methyl derivatives (VIIa) and (VIIb), respectively.