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2004
Multi-membered N-heterocycles
R 0690
Diastereoselective Synthesis of Substituted 2,3,4,5-Tetrahydro-1H-1-benzaEsters by a Tandem Reduction-Reductive Amination Reac52- 143 zepine-5-carboxylic
tion. — An efficient synthesis of tetrahydrobenzazepine derivatives is developed using
a
reduction—reductive amination strategy. Reactions furnishing 2-alkyl-tetrahydrobenzazepine-5-carboxylate proceed diastereoselectively favoring the cis-isomers
(VIII). Attempted reduction—lactamization of nitro diester (VIId) gives amino diester
(XI), which requires further heating for ring closure. — (BUNCE*, R. A.; JOHNSON,
L. B.; HOLT, E. M.; J. Heterocycl. Chem. 41 (2004) 4, 563-568; Dep. Chem., Okla.
State Univ., Stillwater, OK 74078, USA; Eng.) — R. Staver
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