20012-08-2Relevant articles and documents
Aryne-Mediated Arylation of the 3-Benzazepine Scaffold: One-Pot Synthesis of 1-Aryl-3-methyl-2,3,4,5-tetrahydro-1 H -3-benzazepines
Singh, Kamal Nain,Singh, Paramjit,Sharma, Esha,Kaur, Manjot,Deol, Yadwinder Singh
, p. 3212 - 3220 (2015/10/19)
The coupling of β-amino carbanions derived from 3-benzA"azeA"pines with in situ generated arynes has been demonstrated as a convenient route for the direct synthesis of a variety of 1-aryl-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepines, including the biologically active drug molecule SCH 12679.
Rearrangements of 1,6,7-Trisubstituted 2-Methyl-1,2,3,4-tetrahydroisoquinolinium 2-Methylides
Sato, Yoshiro,Shirai, Naohiro,Machida, Yoshio,Ito, Emiko,Yasui, Takayo,et al.
, p. 6711 - 6716 (2007/10/02)
Chemical behavior of 1,6,7-trisubstituted 2-methy-1,2,3,4-tetrahydroisoquinolinium 2-methylides 4 was investigated in fluoride-ion induced desilation reaction of 1,6,7-trisubstituted 2-methyl-2-(trimethylsilyl)methyl-1,2,3,4-tetrahydroisoquinolinium iodid
Tricarbonylchromium(0) Promoted Stereoselective Cyclisations of the N-3,4-Dimethoxyphenethyl Derivatives of the 1-Phenyl Ethanolamines Halostachine, Ephedrine and Pseudoephedrine to 1-Phenyl-N-Methyl-7,8-Dimethoxy-1,2,4,5-Tetrahydrobenzazepines
Coote, Steven J.,Davies, Stephen G.,Middlemiss, David,Naylor, Alan
, p. 33 - 56 (2007/10/02)
Acid promoted cyclisation of homochiral (R)-N-(3,4-dimethoxyphenethyl)-halostachine proceeds with almost total racemisation to yield 1-phenyl-N-methyl-1,2,4,5-tetrahydrobenzazepine (e.e, 6percent).Coordination of the cyclisation precursor to the tricarbonylchromium(0) moiety renders the cyclisation completely stereospecific to afford, after decomplexation, homochiral (+)-(R)-1-phenyl-N-methyl-1,2,4,5-tetrahydrobenzazepine. (-)-(1R,2S)-N-(3,4-Dimethoxyphenethyl)ephedrine undergoes acid mediated cyclisation to furnish trans-(-)-(1R,2S)-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine as a single diastereoisomer.In contrast, the epimeric cyclisation precursor (-)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudoephedrine cyclises to give a mixture (ratio 91:9) of trans- and cis-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine.However, cyclisation of the tricarbonylchromium(0) complex of (-)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudo-ephedrine is completely stereoselective to yield trans-(+)-(1S,2R)-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine after decomplexation.