Cyclization of aryl 3-aryl propynoates into 4-arylcoumarins catalyzed by cyclometalated Platinum(II) complexes

被引：8

作者：

Zaitceva, Olesia ^{[1
,3
]}

Beneteau, Valerie ^{[1
]}

Ryabukhin, Dmitry S. ^{[3
]}

Eliseev, Ivan I. ^{[2
]}

Kinzhalov, Mikhal A. ^{[2
]}

Louis, Benoit ^{[1
,4
]}

Vasilyev, Aleksander V. ^{[2
,3
]}

Pale, Patrick ^{[1
]}

机构：

[1] Univ Strasbourg, Inst Chim, UMR 7177, CNRS, 4 Rue B Pascal, F-67000 Strasbourg, France

[2] St Petersburg State Univ, 7-9 Univ Skaya Nab, St Petersburg 199034, Russia

[3] St Petersburg State Forest Tech Univ, 5 Inst Skii Per, St Petersburg 194021, Russia

[4] Univ Strasbourg, Inst Chim & Proc Energie Environm & Sante, ECPM, 25 Rue Becquerel, F-67087 Strasbourg 2, France

来源：

TETRAHEDRON | 2020年 / 76卷 / 14期

基金：

俄罗斯科学基金会;

关键词：

Coumarin; Cyclization; Platinacycle; Platinum; Catalysis; C-H BONDS; INTRAMOLECULAR HYDROARYLATION; COUMARIN DERIVATIVES; MEDICINAL CHEMISTRY; CONVERSION; ACETYLENE; EFFICIENT; GOLD(III); POLYMERS; ALKYNES;

D O I：

10.1016/j.tet.2020.131029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclometalated (ppy)Pt-II complexes (ppy = 2-phenylpyridinato-C-2,N) catalyze the intramolecular cyclization of aryl propynoates to form coumarins and benzocoumarins. The complex [(ppy)PtCl(MeCN)] (5 mol %) was the most active and efficient catalyst for such reaction, especially in the presence of AgSbF6 (15 mol %) in 1,2-dichloroethane. With this catalytic system, a wide range of substituents and functional groups proved compatible with the cyclization process, leading to a large variety of substituted coumarins and benzocoumarins (22 examples, 77-99%) (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：9

共 50 条

[1] SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF 4-ARYL-3,4-DIHYDROCOUMARINS AND 4-ARYLCOUMARINS
Sun, Jie
Ding, Wei-Xian
Hong, Xiao-Ping
Zhang, Ke-Yun
Zou, Yong
CHEMISTRY OF NATURAL COMPOUNDS, 2012, 48 (01) : 16 - 22
[2] Antioxidant and antitumor activities of 4-arylcoumarins and 4-aryl-3,4-dihydrocoumarins
Zhang, Keyun
Ding, Weixian
Sun, Jie
Zhang, Bin
Lu, Fujiao
Lai, Ren
Zou, Yong
Yedid, Gabriel
BIOCHIMIE, 2014, 107 : 203 - 210
[3] Synthesis and antimicrobial activities of 4-aryl-3,4-dihydrocoumarins and 4-arylcoumarins
Jie Sun
Wei-Xian Ding
Xiao-Ping Hong
Ke-Yun Zhang
Yong Zou
Chemistry of Natural Compounds, 2012, 48 : 16 - 22
[4] Synthesis and characterisation of some nickel(II) complexes with 3-aryl substituted amidinothioureas
George, A
Mathew, A
Alaudeen, M
ASIAN JOURNAL OF CHEMISTRY, 2003, 15 (01) : 315 - 320
[5] Palladium-Catalyzed Asymmetric Benzylation of 3-Aryl Oxindoles
Trost, Barry M.
Czabaniuk, Lara C.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (44) : 15534 - 15536
[6] Cyclometalated Platinum(II) Complexes with 10-(Aryl)phenoxarsine Ligands: Synthesis, Structure, and Photophysical Properties
Galimova, Milyausha F. F.
Kondrashova, Svetlana A. A.
Latypov, Shamil K. K.
Dobrynin, Alexey B. B.
Zueva, Ekaterina M. M.
Petrova, Maria M. M.
Kolesnikov, Ilya E. E.
Musin, Rustem R. R.
Musina, Elvira I. I.
Karasik, Andrey A. A.
ORGANOMETALLICS, 2023, 42 (18) : 2661 - 2671
[7] Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles
Bi, Ming-Xi
Liu, Shuai
Huang, Yangen
Xu, Xiu-Hua
Qing, Feng-Ling
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 657 - 662
[8] Efficient Iodine-catalyzed Synthesis of 3-Aryl 4(3H)-quinazolinones
Wang, Min
Song, Zhi-Guo
Zhang, Ting-Ting
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2010, 42 (02) : 169 - 173
[9] Synthesis of 4-arylcoumarins via palladium-catalyzed arylation/cyclization of ortho-hydroxylcinnamates with diaryliodonium salts
Yang, Yang
Han, Jianwei
Wu, Xunshen
Xu, Shujia
Wang, Limin
TETRAHEDRON LETTERS, 2015, 56 (24) : 3809 - 3812
[10] Palladium catalyzed Heck-arylation/cyclization cascade: An environmentally benign and efficient synthesis of 4-arylcoumarins in water
Chen, Junmin
Liu, Wei
Zhou, Liandi
Zhao, Yongli
TETRAHEDRON LETTERS, 2018, 59 (26) : 2526 - 2531

← 1 2 3 4 5 →