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

被引：20

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

页码：6662 / 6670

页数：9

共 60 条

[1] Flavonoids from Dalbergia louvelii and their antiplasmodial activity
Beldjoudi, N
Mambu, L
Labaïed, M
Grellier, P
Ramanitrahasimbola, D
Rasoanaivo, P
Martin, MT
Frappier, F
[J]. JOURNAL OF NATURAL PRODUCTS, 2003, 66 (11): : 1447 - 1450
[2] Cytotoxic effects, alkylating properties and molecular modelling of coumarin derivatives and their phosphonic analogues
Budzisz, E
Brzezinska, E
Krajewska, U
Rozalski, M
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (06) : 597 - 603
[3] The Emergence of Quinone Methides in Asymmetric Organocatalysis
Caruana, Lorenzo
Fochi, Mariafrancesca
Bernardi, Luca
[J]. MOLECULES, 2015, 20 (07): : 11733 - 11764
[4] A New Organocatalytic Concept for Asymmetric α-Alkylation of Aldehydes
Caruana, Lorenzo
Kniep, Florian
Johansen, Tore Kiilerich
Poulsen, Pernille H.
Jorgensen, Karl Anker
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (45) : 15929 - 15932
[5] Advances in Organocatalytic 1,6-Addition Reactions: Enantioselective Construction of Remote Stereogenic Centers
Chauhan, Pankaj
Kaya, Ugur
Enders, Dieter
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (06) : 888 - 912
[6] 2,3,4-trimethyl-5,7-dihydroxy-2,3-dihydrobenzofuran, a novel antioxidant, from Penicillium citrinum F5
Chen, CH
Shaw, CY
Chen, CC
Tsai, YC
[J]. JOURNAL OF NATURAL PRODUCTS, 2002, 65 (05): : 740 - 741
[7] Enantioselective Reactions of 2-Sulfonylalkyl Phenols with Allenic Esters: Dynamic Kinetic Resolution and [4+2] Cycloaddition Involving ortho-Quinone Methide Intermediates
Chen, Ping
Wang, Kai
Guo, Wengang
Liu, Xianghui
Liu, Yan
Li, Can
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (13) : 3689 - 3693
[8] Asymmetric Catalytic 1,6-Conjugate Addition/Aromatization of para-Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic Centers
Chu, Wen-Dao
Zhang, Le-Fen
Bao, Xu
Zhao, Xian-He
Zeng, Chao
Du, Ji-Yuan
Zhang, Guo-Biao
Wang, Fang-Xin
Ma, Xiao-Yan
Fan, Chun-An
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9229 - 9233
[9] Bifunctional tertiary amine-squaramide catalyzed asymmetric catalytic 1,6-conjugate addition/aromatization of para-quinone methides with oxindoles
Deng, Yu-Hua
Zhang, Xiang-Zhi
Yu, Ke-Yin
Yan, Xu
Du, Ji-Yuan
Huang, Hanmin
Fan, Chun-An
[J]. CHEMICAL COMMUNICATIONS, 2016, 52 (22) : 4183 - 4186
[10] Phosphoric Acid Catalyzed Asymmetric 1,6-Conjugate Addition of Thioacetic Acid to para-Quinone Methides
Dong, Nan
Zhang, Zhi-Pei
Xue, Xiao-Song
Li, Xin
Cheng, Jin-Pei
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (04) : 1460 - 1464

← 1 2 3 4 5 6 →