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A ZnCl 2 ‐Catalyzed Knoevenagel Condensation/1,5‐Hydride Shift/Cyclization Sequence: Synthesis of Novel Spiroisoxazol‐5‐one Tetrahydroquinolines
Author(s) -
Zhao Tuan,
Zhang Huanrui,
Cui Longchen,
Wang Changxue,
Qu Jingping,
Wang Baomin
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600823
Subject(s) - knoevenagel condensation , chemistry , hydride , catalysis , sequence (biology) , yield (engineering) , stereoselectivity , combinatorial chemistry , condensation , organic chemistry , scope (computer science) , hydrogen , materials science , physics , computer science , biochemistry , metallurgy , thermodynamics , programming language
A concise synthesis of novel spiroisoxazol‐5‐one tetrahydroquinoline derivatives has been developed by an efficient ZnCl 2 ‐catalyzed stereoselective Knoevenagel Condensation/1,5‐hydride shift/cyclization sequence. The reactions are broad in scope and the products could be obtained in good to high yields (up to 97 % yield) with good to excellent diastereoselectivities (up to >95:5 dr). In addition, these products may be converted into novel 5‐hydroxy‐spiroisoxazolines and spiropyrazolones.