Mannich and eschweiler‐clarke reaction of 1‐benzyl‐1,2,3,4‐tetrahydroisoquinolines. Studies on the syntheses of heterocyclic compounds. Part CCCXVIII | Zendy

Kametani T. | Zendy; Noguchi I. | Zendy; Saito K. | Zendy

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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.

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