Synthesis 2015; 47(20): 3212-3220
DOI: 10.1055/s-0034-1380453
paper
© Georg Thieme Verlag Stuttgart · New York

Aryne-Mediated Arylation of the 3-Benzazepine Scaffold: One-Pot Synthesis of 1-Aryl-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepines

Kamal Nain Singh*
Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India   eMail: kns@pu.ac.in
,
Paramjit Singh
Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India   eMail: kns@pu.ac.in
,
Esha Sharma
Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India   eMail: kns@pu.ac.in
,
Manjot Kaur
Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India   eMail: kns@pu.ac.in
,
Yadwinder Singh Deol
Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India   eMail: kns@pu.ac.in
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Publikationsverlauf

Received: 10. Februar 2015

Accepted after revision: 05. Mai 2015

Publikationsdatum:
09. Juli 2015 (online)


Abstract

The coupling of β-amino carbanions derived from 3-benz­aze­pines 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.

Supporting Information