Copper-catalyzed γ-selective yne-allylic substitution of vinyl ethynylethylene carbonates towards a formal [3+3] cycloaddition

被引：1

作者：

Bao, Yu ^{[1
]}

Zhu, Haihui ^{[1
]}

Huang, Hai ^{[1
]}

机构：

[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Jiangsu, Peoples R China

来源：

TETRAHEDRON LETTERS | 2025年 / 158卷

关键词：

Vinyl ethynylethylene carbonates; Yne-allylic substitution; 4; H; -Pyrans; Spirocyclic compounds; DERIVATIVES; ESTERS; AGENTS; PYRAN;

D O I：

10.1016/j.tetlet.2025.155487

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Selective nonclassic propargylic substitutions have been a research focus in recent years. Herein, we developed a tandem gamma-selective propargylic substitution and ring closure reaction of vinyl ethynylethylene carbonates (VEECs), efficiently synthesizing a series of 4H-pyran compounds. Additionally, the synthetic applications demonstrated that the products have significant synthetic potential in the synthesis of spirocyclic compounds.

引用

收藏

页数：5

相关论文

共 37 条

[1]

Ahluwalia VK, 1997, INDIAN J CHEM B, V36, P88

[2]

Artizzu N, 1995, FARMACO, V50, P853

[3] SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF PYRAN OXYGEN AND AMIDE NITROGEN REPLACEMENT ANALOGS OF THE POTASSIUM CHANNEL ACTIVATOR CROMAKALIM [J].

ASHWOOD, VA ;

CASSIDY, F ;

EVANS, JM ;

GAGLIARDI, S ;

STEMP, G .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (11) :3261-3267

[4] SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 2-OXO-(2H) 1-BENZOPYRAN-3-CARBOXAMIDE DERIVATIVES [J].

BONSIGNORE, L ;

LOY, G ;

SECCI, D ;

CALIGNANO, A .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (06) :517-520

[5] Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates [J].

Butt, Nicholas A. ;

Zhang, Wanbin .

CHEMICAL SOCIETY REVIEWS, 2015, 44 (22) :7929-7967

[6] STRUCTURE-ACTIVITY CORRELATIONS FOR A SERIES OF ANTIALLERGY AGENTS - OXANILIC, QUINALDIC, AND BENZOPYRAN-2-CARBOXYLIC ACIDS [J].

CHENEY, BV ;

WRIGHT, JB ;

HALL, CM ;

JOHNSON, HG ;

CHRISTOFFERSEN, RE .

JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (09) :936-940

[7] Divergent Gold Catalysis: Unlocking Molecular Diversity through Catalyst Control [J].

Chintawar, Chetan C. ;

Yadav, Amit K. ;

Kumar, Anil ;

Sancheti, Shashank P. ;

Patil, Nitin T. .

CHEMICAL REVIEWS, 2021, 121 (14) :8478-8558

[8] Design and synthesis of novel potent anticoagulant and anti-tyrosinase pyranopyrimidines and pyranotriazolopyrimidines: Insights from molecular docking and SAR analysis [J].

Debbabi, Meriem ;

Nimbarte, Vijaykumar D. ;

Chekir, Samia ;

Chortani, Sarra ;

Romdhane, Anis ;

Ben Jannet, Hichem .

BIOORGANIC CHEMISTRY, 2019, 82 :129-138

[9] Synthesis of pyran and pyranone natural products [J].

Donner, CD ;

Gill, M ;

Tewierik, LM .

MOLECULES, 2004, 9 (06) :498-512

[10] Chemotaxis of Molecular Dyes in Polymer Gradients in Solution [J].

Guha, Rajarshi ;

Mohajerani, Farzad ;

Collins, Matthew ;

Ghosh, Subhadip ;

Sen, Ayusman ;

Velegol, Darrell .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (44) :15588-15591

← 1 2 3 4 →