2-Iodoxybenzoic Acid-Dimethyl Sulfoxide (IBX-DMSO)-Promoted Oxidative Aromatization of Spiro[2.5]octa-4,7-dien-6-one

被引:1
|
作者
Li, Tong [1 ]
Cui, Chaoxing [1 ]
Zhang, Yuxia [2 ]
Song, Xixi [1 ]
Wang, Zechao [3 ]
Chang, Junbiao [1 ]
机构
[1] Zhengzhou Univ, Coll Chem, 100 Sci Ave, Zhengzhou 450001, Peoples R China
[2] Zhengzhou Univ Aeronaut, Sch Math, 15 Wenyuan West Rd, Zhengzhou 450046, Peoples R China
[3] Zhengzhou Univ, Henan Inst Adv Technol, Div Mol Catalysis & Synth, Zhengzhou 450001, Peoples R China
关键词
metal-free reaction; iodoxybenzoic add; dimethyl sulfoxide; oxidation; aromatization; spirooctadienones; AEROBIC OXIDATION; PRIMARY ALCOHOLS; CATALYST SYSTEM; N-HETEROCYCLES; IBX; CYCLIZATION; ALDEHYDES; SOLVENT; REAGENT; DEHYDROGENATION;
D O I
10.1055/a-1863-8862
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A 2-iodoxybenzoic acid (IBX)-dimethyl sulfoxide (IBX-DM-50)-promoted oxidative aromatization of spiro[2.5]octa-4,7-dien-6-ones has been developed. A series of substrates with various substitutions were transformed into oxidative aromatization products in good to excellent yields. This oxidative aromatization features environmentally friendly reagents, high efficiency, a broad substrate scope, broad functional-group tolerance, and mild reaction conditions.
引用
收藏
页码:1546 / 1550
页数:5
相关论文
共 7 条
  • [1] 1,6-Conjugated Addition-Mediated [2+1] Annulation: Approach to Spiro[2.5]octa-4,7-dien-6-one
    Yuan, Zhenbo
    Fang, Xinxin
    Li, Xuanyi
    Wu, Jie
    Yao, Hequan
    Lin, Aijun
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21): : 11123 - 11130
  • [2] Novel living polymerization of 5,7-dichloro-1-oxaspiro[2.5]octa-4,7-dien-6-one
    Dept. of Chemistry for Materials, Mie University, Tsu 514-8507, Japan
    Macromolecules, 12 (3833-3836):
  • [3] A novel living polymerization of 5,7-dichloro-1-oxaspiro[2.5]octa-4,7-dien-6-one
    Kubo, M
    Hara, S
    Shibayama, K
    Itoh, T
    MACROMOLECULES, 1999, 32 (12) : 3833 - 3836
  • [4] Synthesis of spiro[2.5]octa-4,7-dien-6-one with consecutive quaternary centers via 1,6-conjugate addition induced dearomatization of para-quinone methides
    Gai, Kuo
    Fang, Xinxin
    Li, Xuanyi
    Xu, Jinyi
    Wu, Xiaoming
    Lin, Aijun
    Yao, Hequan
    CHEMICAL COMMUNICATIONS, 2015, 51 (87) : 15831 - 15834
  • [5] PHOTOLYSIS OF SPIRO[2.5)OCTA-4,7-DIEN-6-1 . RADICAL FRAGMENTATION IN PHOTOCHEMISTRY OF 2,5-CYCLOHEXADIENONES
    SCHUSTER, DI
    POLOWCZY.CJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (08) : 1722 - &
  • [6] Radical ion probes.: 8.: Direct and indirect electrochemistry of 5,7-di-tert-butylspiro[2.5]octa-4,7-dien-6-one and derivatives
    Phillips, JP
    Gillmore, JG
    Schwartz, P
    Brammer, LE
    Berger, DJ
    Tanko, JM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (01) : 195 - 202
  • [7] Radical ion probes. 11. Reaction of 1,1-dimethyl-5,7-di-t-butylspiro[2.5]octa-4,7-dien-6-one with 5-hexenyl magnesium bromide
    Gillmore, JG
    Tanko, JM
    TETRAHEDRON LETTERS, 1998, 39 (48) : 8795 - 8798