Synthesis of Malononitrile-Substituted Diarylmethines via 1,6-Addition of Masked Acyl Cyanides to para-Quinone Methides

被引：22

作者：

Zhao, Kun ^{[1
]}

Zhi, Ying ^{[1
]}

Wang, Ai ^{[2
]}

Enders, Dieter ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] Rhein Westfal TH Aachen, Inst Inorgan Chem, Landoltweg 1, D-52074 Aachen, Germany

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 04期

关键词：

diarylmethines; 1,6-addition; masked acyl cyanides; para-quinone methides; malononitrile-substituted diarylmethines; ASYMMETRIC 1,6-CONJUGATE ADDITION; EXPEDIENT ACCESS; BOND FORMATION; ACID; ESTERS; ALDEHYDES; ADDITION/AROMATIZATION; CONSTRUCTION; DERIVATIVES; CARBANIONS;

D O I：

10.1055/s-0036-1590947

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the synthesis of malononitrile-substituted diarylmethines through 1,6-conjugate addition of paraquinone methides with masked acyl cyanide (MAC) reagents has been developed. Under mild conditions, the scalable reaction occurs in good to excellent yields providing a straightforward access to a series of malononitrile-substituted diarylmethines. The synthetic utility of this protocol has been demonstrated in the synthesis of bioactive compounds.

引用

页码：872 / 880

页数：9

共 50 条

[31] Acid-Catalyzed Regioselective Synthesis of α-Diarylmethyl Substituted Phenols and para-Quinone Methides in Water
Xiong, Biquan
Shang, Wenli
Xu, Weifeng
Liu, Yu
Tang, Ke-Wen
Wong, Wai-Yeung
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (08)
[32] Direct access to a,a′-diarylated ketones through N-heterocyclic carbene-catalyzed 1,6-addition of aromatic aldehydes to para-quinone methides
Zhang, Guifu
Jiang, Longxiang
Shi, Wenjuan
Zhou, Meiling
Qiu, Fenghao
Sun, Shaofa
Wang, Jian
Guo, Haibing
SYNTHETIC COMMUNICATIONS, 2017, 47 (08) : 803 - 810
[33] Base-Catalyzed Stereoselective 1,6-Conjugated Addition/Aromatization of P(O)-H Compounds with para-Quinone Methides
Xiong, Biquan
Wang, Gang
Zhou, Congshan
Liu, Yu
Xu, Weifeng
Xu, Wen-Yuan
Yang, Chang-An
Tang, Ke-Wen
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (20) : 3273 - 3282
[34] Synthesis of chromeno[4,3-b]pyrrolidines from azomethine ylides and vinyl para-quinone methides via (3?+?2) cycloaddition/oxa-1,6-addition
Wu, Pei-Shan
Liou, Yan-Cheng
Marri, Gangababu
Chen, Yi-Ru
Wu, Jia-Rong
Lin, Wenwei
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2023, 70 (12) : 2136 - 2146
[35] Catalyst-free 1,6-Conjugate Addition of S-Nucleophiles to para-Quinone Methides
Xie, Lei
Zang, Xuyang
Liu, Wanxing
Wu, Ping
Wang, Zhaoxue
Zhao, Chenyi
Gao, Zhenzhen
Li, Xiaojing
Nie, Shaozhen
Wu, Lingang
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (12)
[36] 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
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (04) : 1460 - 1464
[37] 1,6-Conjugate addition of zinc alkyls to para-quinone methides in a continuous-flow microreactor
Jadhav, Abhijeet S.
Anand, Ramasamy Vijaya
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (01) : 56 - 60
[38] Decarboxylative 1,6-Conjugate Addition of α-Keto Acids with Para-Quinone Methides Enabled by Photoredox Catalysis
Wu Zijun
Wang Jian
ACTA CHIMICA SINICA, 2017, 75 (01) : 74 - 79
[39] High diastereoselective synthesis of spiro-barbituratechromans via domino oxa-Michael/1,6-addition reactions of ortho-hydroxyphenylsubstituted para-quinone methides with barbiturate-based olefins
Huo, Mingming
Zhou, Jing
Bai, Lijuan
Xu, Qigui
Zhou, Zhihong
Zhou, Hui
Liang, Guojuan
TETRAHEDRON, 2019, 75 (51)
[40] Dearomatization of 2,3-Disubstituted Indoles via 1,8-Addition of Propargylic (Aza)-para-Quinone Methides
Pan, Han-Peng
Zhu, Zhi-Qiang
Qiu, Zong-Wang
Liu, Hong-Fu
Ma, Jiong-Dong
Li, Bao Qiong
Feng, Na
Ma, Ai-Jun
Peng, Jin-Bao
Zhang, Xiang-Zhi
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23) : 16518 - 16534

← 1 2 3 4 5 →