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One Pot Synthesis of Medicinally Important cis ‐2‐Methyl‐4‐amino substituted‐1,2,3,4‐tetrahydroquinolines
Author(s) -
Kiran Kumar H. C.,
Mahadevan K. M.,
Prabhakara Varma P.,
Srinivasa A.
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201100180
Subject(s) - chemistry , carbazole , acetonitrile , selectivity , solvent , two dimensional nuclear magnetic resonance spectroscopy , catalysis , organic chemistry , proton nmr , stereochemistry , combinatorial chemistry
A simple synthesis of medicinally important cis ‐2‐methyl‐4‐azapan‐2‐one‐1,2,3,4‐tetrahydroquinolines/ cis ‐9‐(2‐methyl‐1,2,3,4‐tetrahydroquinolin‐4‐yl)‐9 H ‐carbazole was reported. Multicomponent one pot synthesis with anilines and N ‐vinylcaprolactam/ N ‐vinyl carbazole via imino Diels‐Alder reaction by using antimony trichloride as catalyst and acetonitrile as solvent was employed. NMR technique (2D) was used to study the regio‐ and stereo‐chemistry of newly synthesized compounds. The cis diastereo‐selectivity of the products was predicted by COSY and NOESY studies.