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Expedient Synthesis of Dihydroisoquinolines by Cascade Annulation of Nitrovinylbenzoquinone
Author(s) -
Zhao Sihan,
Cheng Shaobing,
Liu Hui,
Zhang Jiayan,
Yuan Weicheng,
Zhang Xiaomei
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202000589
Subject(s) - annulation , cascade , chemistry , natural product , combinatorial chemistry , continuation , quinone , product (mathematics) , catalysis , stereochemistry , computer science , mathematics , organic chemistry , programming language , geometry , chromatography
1,2‐Dihydroisoquinolines are important building blocks of many natural products and phamarceuticals. In continuation of our ongoing research on transformations of quinone derivatives, herein we present a catalyst‐free cascade annulation of β ‐enamino esters with 2‐(2‐nitrovinyl)‐1,4‐benzoquinone, which allowed for the synthesis of various novel 1,2‐dihydroisoquinoline derivatives in moderate to good yields (60 %–99 %). This method is applicable to a wide variety of β ‐enamino esters. The structure of one product was determined by an x‐ray crystal analysis. Moreover, a plausible mechanism was proposed.