Iron-Catalyzed One-Step Synthesis of Isothiazolone/1,2-Selenazolone Derivatives via [3+1+1] Annulation of Cyclopropenones, Anilines, and Elemental Chalcogens

被引:4
作者
Wang, Hongchen [1 ]
Yan, Rulong [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
Isothiazolone /1,2-Selenazolone derivatives; Cyclopropenone; Elemental chalcogens; Cyclization; S BOND FORMATION; ANTIMICROBIAL ACTIVITY; TRIFLIC ANHYDRIDE; INHIBITORS; THIAZOLES; 1,2-BENZISOTHIAZOL-3(2H)-ONES; FUNCTIONALIZATION; ISOTHIAZOLES; CYCLIZATION; ACTIVATION;
D O I
10.1002/adsc.202101175
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Described herein is the one-step synthesis of isothiazolone/1,2-selenazolone derivatives via [3+1+1] cycloaddition of cyclopropenone derivatives, anilines, and elemental chalcogens. The cascade reaction involves the C-S, C-N, and N-S bond formation along with the cleavage of C-C bond. Both anilines and cyclopropenones are tolerated and give the corresponding products in 28-73% yields.
引用
收藏
页码:715 / 719
页数:5
相关论文
共 39 条
[31]   One-Pot Synthesis of Triazolothiadiazepine 1,1-Dioxide Derivatives via Copper-Catalyzed Tandem [3+2] Cycloaddition/N-Arylation [J].
Barange, Deepak Kumar ;
Tu, Yu-Chen ;
Kavala, Veerababurao ;
Kuo, Chun-Wei ;
Yao, Ching-Fa .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (01) :41-48
[32]   Efficient one-step synthesis of 3-(indol-2-yl)quinoxalin-2(1H)-ones via electrochemical oxidative cross-dehydrogenative coupling [J].
Zhang, Hao ;
Hu, Lishan ;
Yu, Kai ;
Lou, Lan-Lan ;
Liu, Shuangxi .
NEW JOURNAL OF CHEMISTRY, 2022, 46 (17) :8037-8042
[33]   Facile one-pot synthesis of 2,3-dihydro-1H-indolizinium derivatives by rhodium(III)-catalyzed intramolecular oxidative annulation via C-H activation: application to ficuseptine synthesis [J].
Upadhyay, Nitinkumar Satyadev ;
Jayakumar, Jayachandran ;
Cheng, Chien-Hong .
CHEMICAL COMMUNICATIONS, 2017, 53 (16) :2491-2494
[34]   Iodine-catalyzed synthesis of 5-benzoyl-8H-phthalazino[1,2-b] quinazolin-8-one derivatives via a domino reaction involving a benzyl automatic oxidation by oxygen [J].
Liu, Jian-Quan ;
Feng, Bin-Bin ;
Wang, Xiang-Shan .
TETRAHEDRON, 2018, 74 (36) :4746-4753
[35]   Efficient synthesis of 4-(3′-furanyl)butenolide derivatives via PdII-catalyzed oxidative heterodimeric cyclization reaction of 2,3-allenoic acids and 1,2-allenyl ketones [J].
Ma, SM ;
Yu, ZQ .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (08) :2078-2087
[36]   Synthesis of Oxindoles by Iron-Catalyzed Oxidative 1,2-Alkylarylation of Activated Alkenes with an Aryl C(sp2)H Bond and a C(sp3)H Bond Adjacent to a Heteroatom [J].
Wei, Wen-Ting ;
Zhou, Ming-Bo ;
Fan, Jian-Hong ;
Liu, Wei ;
Song, Ren-Jie ;
Liu, Yu ;
Hu, Ming ;
Xie, Peng ;
Li, Jin-Heng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (13) :3638-3641
[37]   Regio- and diastereoselective synthesis of 3,4-dihydro-2H-benzo [4,5] imidazo[2,1-b] [1,3]thiazine derivatives via DBU-catalyzed [3+3] annulation of MBH carbonates with 2-mercaptobenzimidazoles [J].
Jiang, Lin ;
Peng, Peiying ;
Yu, Liudong ;
Jiang, Dengbang ;
Wang, Yidan ;
Li, Hongli ;
Yuan, Minglong ;
Yuan, Mingwei .
TETRAHEDRON, 2021, 98
[38]   Synthesis of (Z)-1,2-dihydro-1-tosylbenzo[b]azepin-3-ones by two-step, one-pot gold-catalyzed tandem heterocyclization/Petasis-Ferrier rearrangement of 2-(N-(prop-2-ynyl)-N-tosylamino)benzaldehydes [J].
Sze, Ella Min Ling ;
Koh, Ming Joo ;
Tjia, Yen Min ;
Rao, Weidong ;
Chan, Philip Wai Hong .
TETRAHEDRON, 2013, 69 (26) :5558-5565
[39]   ONE-STEP SYNTHESIS OF 4H-3,1-BENZOXAZIN-4-ONES FROM WEINREB AMIDES AND 1,4,2-DIOXAZOL-5-ONES VIA COBALT-CATALYZED C-H BOND ACTIVATION [J].
Tanimoto, Iku ;
Kawai, Kentaro ;
Sato, Akane ;
Yoshino, Tatsuhiko ;
Matsunaga, Shigeki .
HETEROCYCLES, 2019, 99 (01) :118-125