Organocatalytic [4+2] cyclizations of para-quinone methide derivatives with isocyanates

被引：19

作者：

Cheng, Yu-Chun ^{[1
]}

Wang, Cong-Shuai ^{[1
]}

Li, Tian-Zhen ^{[1
]}

Gao, Feng ^{[1
]}

Jiao, Yinchun ^{[2
]}

Shi, Feng ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China

[2] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 27期

关键词：

CATALYTIC 1,6-CONJUGATE ADDITION/AROMATIZATION; DIELS-ALDER REACTION; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE CONSTRUCTION; COUMARIN DERIVATIVES; ACID; CYCLOADDITION; DIHYDROCOUMARINS; ALKYLATION; ANNULATION;

D O I：

10.1039/c9ob00918c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first [4 + 2] cyclizations of para-quinone methide derivatives with isocyanates have been established under the catalysis of Bronsted acids or Bronsted bases, which efficiently constructed benzoxazin-2-one frameworks in generally high yields (up to 95%). This reaction will not only enrich the research contents of para-quinone methide-involved cyclization reactions but also provide a useful method for constructing biologically important benzoxazin-2-one frameworks.

引用

下载

页码：6662 / 6670

页数：9

共 50 条

[21] QUINONE IMIDES .4. PARA-QUINONE MONOSULFONIMIDES
ADAMS, R
LOOKER, JH
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (03) : 1145 - 1149
[22] Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4+2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and Cyanoalkenes
Dong, Taiwei
Wei, Peifeng
Li, Min
Gao, Feng
Qin, Yuan
FRONTIERS IN CHEMISTRY, 2021, 9
[23] IONIC ASSOCIATION PHENOMENA OF PARA-QUINONE METHIDE RADICAL-ANION SALTS
VECIANA, J
MARTINEZ, AD
ARMET, O
REVIEWS OF CHEMICAL INTERMEDIATES, 1988, 10 (01): : 35 - 70
[24] Chiral Bronsted acid-catalyzed asymmetric intermolecular [4+2] annulation of ynamides with para-quinone methides
Li, Hang-Hao
Meng, Ya-Nan
Chen, Can-Ming
Wang, Yu-Qi
Zhang, Zhi-Xin
Xu, Zhou
Zhou, Bo
Ye, Long-Wu
SCIENCE CHINA-CHEMISTRY, 2023, 66 (05) : 1467 - 1473
[25] [4+2]-Cycloaddition of para-Quinone Methides with Hexahydro-1,3,5-Triazines: Access to 1,3-Benzoxazine Derivatives
Cheng, Xiao
Zhou, Shuang-Jing
Xu, Guo-Yong
Wang, Long
Yang, Qing-Qing
Xuan, Jun
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (03) : 523 - 527
[26] Metal-free and enantioselective synthesis of 1,4-benzoxazepines from para-quinone methide derivatives and α-bromohydroxamates
Qi, Suo-Suo
Luo, Xin
Sun, Xiao-Ping
Zhai, Jing-Jing
Chu, Ming-Ming
Chen, Jin
Wang, Yi-Feng
Xu, Dan-Qian
CHEMICAL COMMUNICATIONS, 2023, 59 (57) : 8822 - 8825
[27] Enantioselective synthesis of triarylmethanes via organocatalytic transfer hydrogenation of para-quinone methides
Han, Zhengyu
Zang, Yu
Liu, Chang
Guo, Wengang
Huang, Hai
Sun, Jianwei
CHEMICAL COMMUNICATIONS, 2022, 58 (51) : 7128 - 7131
[28] C7-Friedel-Crafts alkylation of 4-aminoindoles with para-quinone methide derivatives under catalyst-free conditions
Cai, Lu
Jia, Xian
Zhao, Junling
SYNTHETIC COMMUNICATIONS, 2020, 50 (11) : 1679 - 1686
[29] A facile generation of quinolone quinone methide and its [4+2] cycloaddition to pentafulvenes: Synthesis of novel pyranoquinolinone derivatives
Nair, V
Jayan, CN
Treesa, PM
Mathen, JS
Varma, L
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2001, 40 (11): : 1108 - 1113
[30] [4+2] Cycloaddition reactions of coumarin quinone methide with pentafulvenes: facile synthesis of novel polycyclic pyran derivatives
Nair, V
Jayan, CN
Radhakrishnan, KV
Anilkumar, G
Rath, NP
TETRAHEDRON, 2001, 57 (27) : 5807 - 5813

← 1 2 3 4 5 →