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Multicomponent Reaction for Selective Synthesis of Spiro[indene‐2,7′‐isoquinoline] and 1,2,8,8 a ‐Tetrahydroisoquinoline Derivatives
Author(s) -
Cao Jun,
Sun Jing,
Yan ChaoGuo
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201803715
Subject(s) - malononitrile , isoquinoline , chemistry , indene , piperidine , tetrahydroisoquinoline , ethanol , ring (chemistry) , medicinal chemistry , component (thermodynamics) , organic chemistry , combinatorial chemistry , catalysis , physics , thermodynamics
Abstract The piperidine promoted three‐component reaction of N ‐alkylpiperidin‐4‐ones, malononitrile and 2‐arylidene‐1,3‐indanediones in ethanol selectively resulted in the spiro[indene‐2,7′‐isoquinoline] and the ring‐opened cis ‐ or trans ‐1,2,8,8 a ‐tetrahydroisoquinoline derivatives at room temperature or at the elevated temperature. However, the four‐component reaction N ‐alkylpiperidin‐4‐ones, malononitrile, aromatic aldehydes and 1,3‐indanedione in refluxing ethanol mainly afforded ring‐opened cis ‐1,2,8,8 a ‐tetrahydroisoquinoline derivatives in good yields and with high diastereoselectivity. A plausible domino reaction mechanism was proposed for the formation of the different polycyclic products.