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Intramolecular Pictet–Spengler Reaction of Cyclic Iminium ions: A Novel Access to Benzo[1,4]oxazepine‐Fused Tetrahydroisoquinoline and Tetrahydro‐β‐carboline Analogues
Author(s) -
Unnava Ramanjaneyulu,
Sahu Archana K.,
Saikia Anil K.
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700211
Subject(s) - iminium , chemistry , intramolecular force , tetrahydroisoquinoline , pictet–spengler reaction , trifluoroacetic acid , benzaldehyde , isoquinoline , combinatorial chemistry , ion , stereochemistry , organic chemistry , catalysis
A simple and efficient approach has been developed for the synthesis of benzo[1,4]oxazepino‐fused tetrahydroisoquinoline and tetrahydro‐β‐carboline derivatives via one‐pot cascade reaction sequence. This reaction involves the intramolecular Pictet–Spengler reaction of cyclic iminium ions, which were generated in situ via trifluoroacetic acid (TFA)‐mediated deprotection of an acetal derived from β‐arylethylamines and 2‐(2,2‐diethoxyethoxy)benzaldehyde. All reactions produced a novel library of complex fused polyheterocyclic compounds in good to excellent yields.