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

[31] QUINONE IMIDES .2. PARA-QUINONE DIACYL AND DIAROYLIMIDES
ADAMS, R
ANDERSON, JL
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (11) : 5154 - 5157
[32] Regiospecific oxidation of para-quinone methide precursors for improved phosphodiester alkylation and product stability.
Turnbull, KD
Hudgens, TL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U145 - U145
[33] Organocatalytic Asymmetric Synthesis of Tetrahydroquinolines from ortho-Aminophenyl para-Quinone Methides
Luo, Fengbiao
Dong, Hao
Ren, Weiwu
Wang, Yang
ORGANIC LETTERS, 2022, 24 (42) : 7727 - 7731
[34] Intramolecular [4+2] cycloaddition of a photogenerated o-quinone methide in aqueous solution
Department of Chemistry, Box 3065, University of Victoria, Victoria, BC V8W 3V6, Canada
J. Photochem. Photobiol. A Chem., 1-3 (91-96):
[35] Intramolecular [4+2] cycloaddition of a photogenerated o-quinone methide in aqueous solution
Barker, B
Diao, L
Wan, P
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1997, 104 (1-3) : 91 - 96
[36] Organocatalytic Enantioselective Formal (4+2)-Cycloadditions of Phosphine-Containing Dipoles with Isocyanates
Chen, Xuling
Wang, Tao
Lu, Zhongyue
Li, Pengfei
ORGANIC LETTERS, 2022, 24 (16) : 3102 - 3106
[37] Uranyl-catalyzed hydrosilylation of para-quinone methides: access to diarylmethane derivatives
Yu, Jipan
Chen, Siyu
Liu, Kang
Yuan, Liyong
Mei, Lei
Chai, Zhifang
Shi, Weiqun
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (07) : 1575 - 1579
[38] Synthesis of Quinone Methide Substituted Neonicotinoid Derivatives via 1,6-Conjugate Addition of N-Benzyl Nitro Ketene Aminals with para-Quinone Methides Accompanying Oxidation
Wang, Bao-Qu
Luo, Qin
Xiao, Qiang
Lin, Jun
Yan, Sheng-Jiao
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (09): : 8382 - 8389
[39] Trapping para-Quinone Methide Intermediates with Ferrocene: Synthesis and Preliminary Biological Evaluation of New Phenol-Ferrocene Conjugates
Gonzalez-Pelayo, Silvia
Lopez, Enol
Borge, Javier
de-los-Santos-Alvarez, Noemi
Lopez, Luis A.
MOLECULES, 2018, 23 (06):
[40] Enantioselective Synthesis of Triarylmethanes via Organocatalytic 1,6-Addition of Arylboronic Acids to Para-Quinone Methides
Huang, Gong-Bin
Huang, Wei-Hua
Guo, Jing
Xu, Dong-Liang
Qu, Xiao-Chen
Zhai, Pei-Hong
Zheng, Xiu-Hua
Weng, Jiang
Lu, Gui
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) : 1241 - 1246

← 1 2 3 4 5 →