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Silver(I)‐Catalyzed Regioselective Synthesis of Dihydrofuro[3,4‐ b ]quinolines from o ‐Alkynylquinoline‐MBH Adducts and Evaluation of their Photophysical Properties
Author(s) -
Kumar Vipin,
Tiwari Sandip Kumar,
Singh Virender
Publication year - 2020
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.202000002
Subject(s) - regioselectivity , chemistry , adduct , catalysis , molecule , inert gas , reaction conditions , dig , medicinal chemistry , stereochemistry , organic chemistry , combinatorial chemistry , computer security , computer science
A simple and facile approach is described for the regioselective synthesis of dihydrofuro[3,4‐ b ]quinolines from ortho ‐alkynylquinoline‐Morita‐Baylis‐Hillman adducts under mild reaction conditions. Interestingly, in case of aromatic alkynes, 5 ‐exo‐dig cyclization was observed, while in case of aliphatic long chain alkynes, 6 ‐endo‐dig cyclized products were obtained. The present approach does not require any dry conditions, tedious work‐up or inert atmosphere for the production of dihydrofuro[3,4‐ b ]quinolines. The exact structures and stereochemistry of the synthesized molecules were assigned by NMR and X‐ray crystallographic analysis. Their photophysical properties were also evaluated.