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Construction of Spiropyrido[2, 1‐ a ]isoquinoline via Tandem Reactions of Huisgen's 1,4‐Dipoles with Various Alkene Dipolarophiles
Author(s) -
Zhang YuanYuan,
Han Ying,
Sun Jing,
Yan ChaoGuo
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701348
Subject(s) - isoquinoline , chemistry , dimethyl acetylenedicarboxylate , alkene , acetonitrile , indene , cascade reaction , cycloaddition , medicinal chemistry , tandem , organic chemistry , catalysis , materials science , composite material
Abstract The three‐component reaction of isoquinoline, dimethyl acetylenedicarboxylate and arylidene pivaloylacetonitrile in acetonitrile at room temperature afforded pyrido[2, 1‐ a ]isoquinolines 1 a‐1 j in good yields and with high diastereoselectivity. When arylidene‐substituted 1,3‐indanediones, Meldrum acids, and N,N’ ‐dimethylbarbituric acids were employed in the reaction, the novel functionalized spiro[indene‐2, 1′‐pyrido[2, 1‐ a ]isoquinolines] 2 a‐2 j , spiro[pyrido[2, 1‐ a ]isoquinoline‐1,5′‐[1, 3]dioxanes] 3 a‐3 h and spiro[pyrido[2, 1‐ a ]isoquinoline‐1,5′‐pyrimidines] 4 a‐4 e were also efficiently synthesized in satisfactory yields. The reaction mechanism included domino formation of Huisgen's 1,4‐dipole, Michael addition and cyclization processes.