A ZnCl2‐Catalyzed Knoevenagel Condensation/1, 5‐Hydride Shift/Cyclization Sequence: Synthesis of Novel Spiroisoxazol‐5‐one Tetrahydroquinolines. Issue 13 (22nd August 2016)

• Record Type: Journal Article
• Authors: Zhao, Tuan; Zhang, Huanrui; Cui, Longchen; Wang, Changxue; Qu, Jingping; Wang, Baomin
• Is Part Of: ChemistrySelect. Volume 1:Issue 13(2016)
• Page Start: 3713
• Page End: 3717
• Publication Date: 2016-08-22
• Subjects: 1, 5-H shift -- spiroisoxazol-5-one -- tetrahydroquinoline -- zinc chloride; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201600823
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A concise synthesis of novel spiroisoxazol‐5‐one tetrahydroquinoline derivatives has been developed by an efficient ZnCl2 ‐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. Abstract : A concise synthesis of novel spiroisoxazol‐5‐one tetrahydroquinoline derivatives has been developed by an efficient ZnCl2 ‐catalyzed stereoselective Knoevenagel condensation/1, 5‐hydride shift/cyclization sequence. The reaction is 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, the products may be converted into novel 5‐hydroxy‐spiroisoxazolines and spiropyrazolones.