Base-Promoted 1,6-Aza-Michael Addition of Azauracils to para -Quinone Methides

被引:4
作者
Dash, Rupashri [1 ]
Hota, Sudhir Kumar [1 ]
Murarka, Sandip [1 ]
机构
[1] Indian Inst Technol Jodhpur, Dept Chem, Karwar 342037, Rajasthan, India
来源
SYNTHESIS-STUTTGART | 2024年 / 56卷 / 04期
关键词
azauracil; para-quinone methides; 1,6-addition; aza-Michael; metal-free; CATALYTIC 1,6-CONJUGATE ADDITION/AROMATIZATION; ENANTIOSELECTIVE SYNTHESIS; EXPEDIENT ACCESS; METAL-FREE; 1,6-ADDITION; DERIVATIVES; ALKYLATION; AROMATIZATION; ESTERS; ACID;
D O I
10.1055/a-2104-5943
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report an efficient higher order conjugate addition of azauracils to substituted para-quinone methides (p-QMs) mediated by triethylamine to furnish hitherto unknown diarylmethane scaffolds through construction of a C-N bond. The protocol features mild conditions, high atom economy, and broad scope, and enables convenient access to biologically relevant new chemical entities (NCEs) comprised of p-QM and azauracil hybrids in good to excellent yields.
引用
收藏
页码:677 / 685
页数:9
相关论文
共 63 条
[1]   Catalyst- and reagent-free 1,6-hydrophosphonylation of p-quinone methides: a practical approach for the synthesis of diarylmethyl phosphine oxides [J].
Aher, Yogesh N. ;
Pawar, Amit B. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (32) :7536-7546
[2]   C-N bond forming cross-coupling reactions: an overview [J].
Bariwal, Jitender ;
Van der Eycken, Erik .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) :9283-9303
[3]   A New Organocatalytic Concept for Asymmetric α-Alkylation of Aldehydes [J].
Caruana, Lorenzo ;
Kniep, Florian ;
Johansen, Tore Kiilerich ;
Poulsen, Pernille H. ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (45) :15929-15932
[4]   Catalytic Asymmetric N-Alkylation of Indoles and Carbazoles through 1,6-Conjugate Addition of Aza-para-quinone Methides [J].
Chen, Min ;
Sun, Jianwei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (16) :4583-4587
[5]   Asymmetric Catalytic 1,6-Conjugate Addition/Aromatization of para-Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic Centers [J].
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 .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) :9229-9233
[6]   Interferon, ribavirin, 6-azauridine and glycyrrhizin: antiviral compounds active against pathogenic flaviviruses [J].
Crance, JM ;
Scaramozzino, N ;
Jouan, A ;
Garin, D .
ANTIVIRAL RESEARCH, 2003, 58 (01) :73-79
[7]   Electrochemical Radical δ-H Sulfonylation Reaction for the Synthesis of 4-((Aryl,Arylsul fonyl)methylene)-2,5-Cyclohexadiene Derivatives [J].
Dai, Lei ;
Yu, Qiuyu ;
Zhang, Jinghang ;
Wu, Fan ;
Wang, Chang ;
Zhang, Jinpeng ;
Rong, Liangce .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (15) :10568-10579
[8]   An organophotoredox-catalyzed redox-neutral cascade involving N-(acyloxy)phthalimides and allenamides: synthesis of indoles [J].
Das, Sanju ;
Azim, Aznur ;
Hota, Sudhir Kumar ;
Panda, Satya Prakash ;
Murarka, Sandip ;
De Sarkar, Suman .
CHEMICAL COMMUNICATIONS, 2021, 57 (97) :13130-13133
[9]   An organophotoredox-catalyzed redox-neutral cascade involving N-(acyloxy)phthalimides and maleimides [J].
Das, Sanju ;
Parida, Sushanta Kumar ;
Mandal, Tanumoy ;
Hota, Sudhir Kumar ;
Roy, Lisa ;
De Sarkar, Suman ;
Murarka, Sandip .
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (10) :2256-2262
[10]   Organophotoredox-Catalyzed Cascade Radical Annulation of 2-(Allyloxy)arylaldehydes with N-(acyloxy)phthalimides: Towards Alkylated Chroman-4-one Derivatives [J].
Das, Sanju ;
Parida, Sushanta Kumar ;
Mandal, Tanumoy ;
Sing, Laxmikanta ;
De Sarkar, Suman ;
Murarka, Sandip .
CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (05) :568-572