A ZnCl 2 ‐Catalyzed Knoevenagel Condensation/1,5‐Hydride Shift/Cyclization Sequence: Synthesis of Novel Spiroisoxazol‐5‐one Tetrahydroquinolines | Zendy

Zhao Tuan | Zendy; Zhang Huanrui | Zendy; Cui Longchen | Zendy; Wang Changxue | Zendy; Qu Jingping | Zendy; Wang Baomin | Zendy

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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.

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