20012-08-2Relevant academic research and scientific papers
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.
Direct syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines via hydroamination of enol carbamates
Crecente-Campo, José,Vázquez-Tato, M. Pilar,Seijas, Julio A.
experimental part, p. 2655 - 2659 (2009/06/20)
An efficient and simple procedure for the syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines has been developed. The approach uses easily available starting materials and requires just three steps. The hydroamination of an enol carbamate is the key step. This general and direct method has been applied to the total synthesis of the natural alkaloid cherylline and to biologically active 3-benzoazepines as well.
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
Stereoisomeric probes for the D1 dopamine receptor: synthesis and characterization of R-(+) and S-(-) enantiomers of 3-allyl-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine and its 6-bromo analogue.
Neumeyer,Kula,Baldessarini,Baindur
, p. 1466 - 1471 (2007/10/02)
Substituted 1-phenyl-3-benzazepines (e.g., SKF 38393 and fenoldopam) exhibit stereoselectivity in moderately high-affinity binding to and partial agonist activation of D1 dopamine receptors. The 3-allyl (APB) and the 3-allyl-6-chloro (6-Cl-APB) analogues
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.
ENANTIOSPECIFIC SYNTHESIS OF (+)-(R)-1-PHENYL-3-METHYL-1,2,4,5-TETRAHYDROBENZAZEPINE FROM (+)-(S)-N-METHYL-1-PHENYL ETHANOLAMINE (HALOSTACHINE) via ARENE CHROMIUM TRICARBONYL METHODOLOGY
Coote, Steven J.,Davies, Stephen G.,Middlemiss, David,Naylor, Alan
, p. 3581 - 3584 (2007/10/02)
Acid promoted cyclisation of homochiral (R)-N-(3,4-dimethoxyphenethyl) halostachine chromium tricarbonyl is stereospecific, proceeding with retention of configuration, to afford, after decomplexation, homochiral (+)-(R)-1-phenyl-3-methyl-1,2,4,5-tatrahydr
PHARMACEUTICAL COMPOSITIONS AND METHODS INVOLVING BENZAZEPINE DERIVATIVES
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, (2008/06/13)
Pharmaceutical compositions and a method of stimulating peripheral dopamine receptors by administering internally a nontoxic effective quantity of a benzazepine derivative to an animal. Renal vasodilator and diuretic methods are also disclosed.
Pharmaceutical compositions and method of producing anti-Parkinsonism activity
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, (2008/06/13)
Pharmaceutical compositions and method of producing anti-Parkinsonism activity by administering internally a nontoxic effective quantity of a benzazepine derivative to an animal.
