Organocatalyzed Formal [4+2] Cycloaddition of in situ Generated Azoalkenes with Arylacetic Acids: An Efficient Approach to the Synthesis of 4,5-Dihydropyridazin-3(2H)-ones

被引：35

作者：

Li, Xuanyi ^{[1
,2
]}

Gai, Kuo ^{[1
,2
]}

Yuan, Zhenbo ^{[1
,2
]}

Wu, Jie ^{[1
,2
]}

Lin, Aijun ^{[1
,2
]}

Yao, Hequan ^{[1
,2
]}

机构：

[1] China Pharmaceut Univ, SKLNM, Nanjing 210009, Peoples R China

[2] China Pharmaceut Univ, Sch Pharm, Dept Med Chem, Nanjing 210009, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 16-17期

基金：

中国国家自然科学基金;

关键词：

1,2-diaza-1,3-dienes; 4,5-dihydropyridazin-3(2H)-ones; isothiourea catalysis; DYNAMIC KINETIC RESOLUTION; ASYMMETRIC-SYNTHESIS; ACYL; 1,2-DIAZA-1,3-DIENES; BENZOTETRAMISOLE; LACTONIZATION; ANNULATION; ANHYDRIDES; REACTIVITY; INDOLES;

D O I：

10.1002/adsc.201500645

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An unprecedented [4+2] cycloaddition of in situ generated azoalkenes with arylacetic acids has been developed under the catalysis of isothiourea. The reaction provided an efficient approach to the synthesis of 4,5-dihydropyridazin-3(2H)-one derivatives in moderate to good yields (up to 95%).

引用

页码：3479 / 3484

页数：6

共 45 条

[21] AN EFFICIENT ONE-POT SYNTHESIS OF 4-HYDROXYISOQUINOLINE-1,3(2H,4H)-DIONES FROM N-ALKYLBENZAMIDES AND α-KETO ESTERS
Kobayashi, Kazuhiro
Honda, Yuuya
HETEROCYCLES, 2017, 94 (06) : 1099 - 1106
[22] Formal Acylamination of Nitroalkenes in Aqueous Medium for the Synthesis of 2-Aryl-3-nitro-2,3-dihydroquinolin-4(1H)-ones
Chaturvedi, Atul Kumar
Rastogi, Namrata
SYNTHESIS-STUTTGART, 2015, 47 (02): : 249 - 255
[23] Palladium-catalyzed one-pot cycloaddition reactions of thioureas with 3H-indol-3-ones generated in situ from 2-alkynyl arylazides: rapid and efficient access to imidazoloindolines
Li, Ping
Zhu, Boyu
Xu, Yao
Zhou, Zhiqiang
Hu, Guiwen
Yang, Fan
Xu, Shijie
Zhang, Xiaoxiang
ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (21): : 3480 - 3485
[24] Controllable synthesis of pyrido[2,3-b]indol-4-ones or indolo[3,2-b]quinolines via formal intramolecular C(sp2)-H functionalization
Song, Bo
Wang, Mengdan
Xu, Murong
Kong, Lingkai
Xie, Huihui
Wang, Chengyu
Li, Yanzhong
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (46) : 9960 - 9965
[25] Copper-Catalyzed [3+2] Annulation of O-Acyl Oximes with 4-Sulfonamidophenols for the Synthesis of 5-Sulfonamidoindoles and 2-Amido-5-sulfonamidobenzofuran-3(2H)-ones
Hu, Zi-Jun
Chen, Wei
Lyu, Xinyu
Zhang, Hui-Peng
Chen, Si-Wei
Ding, Xian-Heng
Yu, Cang-Hai
Cui, Zhen
Miao, Chun-Bao
Yang, Hai-Tao
ORGANIC LETTERS, 2024, 26 (20) : 4229 - 4234
[26] Synthesis of 3-Aroylpyrrolo[1,2-a][4,1]benzoxazepine-1,2,4(6H)-triones by the Reaction of 2-(2-Aryl-2-oxoethylidene)-1,5-dihydro-4,1-benzoxazepin-3(2H)-ones with Oxalyl Chloride
Maslivets, A. A.
Dmitriev, M., V
Maslivets, A. N.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 57 (10) : 1608 - 1613
[27] An efficient and green synthesis of 2-phenylquinazolin-4(3H)-ones using Bronsted acidic ionic liquid grafted onto silica
Huynh, Tam Thanh Thi
Nguyen, The Thai
Tran, Phuong Hoang
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2023, 98 (02) : 555 - 565
[28] Enantioselective [4+2] Cycloadditions of 2-Vinyl-1H-indoles with 3-Nitro-2H-chromenes Catalyzed by a Zn(OTf)2/Bis(oxazoline) Complex: An Efficient Approach to Fused Heterocycles with a Quaternary Stereocenter
Tan, Fen
Xiao, Cong
Cheng, Hong-Gang
Wu, Wei
Ding, Ke-Rong
Xiao, Wen-Jing
CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (03) : 493 - 497
[29] Synthesis of 2-(5-nitropyrid-2-yl)-3-(4-substitutedphenyl)aminoisoxazol-5(2H)-ones and their rearrangements to imidazo[1,2-a]-pyridines, and indoles with triethylamine
Khalafy, J
Setamdideh, D
Dilmaghani, KA
MOLECULES, 2002, 7 (12) : 907 - 916
[30] Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones
Nori, Valeria
Arcadi, Antonio
Carlone, Armando
Marinelli, Fabio
Chiarini, Marco
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 1084 - 1091

← 1 2 3 4 5 →