4-Dimethylaminopyridine-catalyzed [3+3] spiroannulation reactions of isatin-derived Morita-Baylis-Hillman carbonates with indoline-2-thiones

被引:12
作者
Geng, Congcong [1 ]
Wei, Xingfu [1 ]
Xu, Yongqiang [1 ]
Liu, Jianhui [1 ]
Peng, Lizeng [2 ]
Wang, Baomin [1 ]
机构
[1] Dalian Univ Technol, Dept Pharmaceut Sci, State Key Lab Fine Chem, Dalian 116024, Peoples R China
[2] Shandong Acad Agr Sci, Jinan 250100, Peoples R China
关键词
Spiroannulations; DMAP; Morita -Baylis -Hillman carbonates; Sulfur heterocycles; ANNULATED SULFUR HETEROCYCLES; STEREOSELECTIVE-SYNTHESIS; CONSTRUCTION; DERIVATIVES; ALKYLATION; ACCESS; THIOPYRANO; SKELETONS; OXINDOLES; ADDUCTS;
D O I
10.1016/j.tetlet.2022.153950
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
DMAP-catalyzed diastereoselective [3 + 3] spiroannulations of isatin-derived Morita-Baylis-Hillman car-bonates with indoline-2-thiones were achieved. A series of bisindole-annulated thiopyran frameworks were synthesized in good yields with good diastereoselectivities. The strategy developed in this paper offered a novel way for the synthesis of valuable indole-annulated sulfur heterocycle derivatives which might be beneficial in organic synthesis and medicinal chemistry. (c) 2022 Elsevier Ltd. All rights reserved.
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页数:4
相关论文
共 45 条
[1]  
ANNAKA M, 1994, HETEROCYCLES, V39, P251
[2]   Stereoselective Synthesis of 3,3-Disubstituted Oxindoles and Spirooxindoles via Allylic Alkylation of Morita-Baylis-Hillman Carbonates of Isatins with Cyclic Sulfamidate Imines Catalyzed by DABCO [J].
Arupula, Sanjeeva K. ;
Guin, Soumitra ;
Yadav, Anubha ;
Mobin, Shaikh M. ;
Samanta, Sampak .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (05) :2660-2675
[3]   Synthesis of tetrahydrothiopyrano[2,3-b]indoles via [3+3] annulation of nitroallylic acetates with indoline-2-thiones [J].
Basu, Pallabita ;
Hazra, Chiranjit ;
Baiju, Thekke, V ;
Namboothiri, Irishi N. N. .
NEW JOURNAL OF CHEMISTRY, 2020, 44 (04) :1389-1399
[4]   The antimicrobial natural product chuangxinmycin and some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase [J].
Brown, MJ ;
Carter, PS ;
Fenwick, AE ;
Fosberry, AP ;
Hamprecht, DW ;
Hibbs, MJ ;
Jarvest, RL ;
Mensah, L ;
Milner, PH ;
O'Hanlon, PJ ;
Pope, AJ ;
Richardson, CM ;
West, A ;
Witty, DR .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (21) :3171-3174
[5]   An insight in anti-malarial potential of indole scaffold: A review [J].
Chauhan, Mehak ;
Saxena, Anjali ;
Saha, Biswajit .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2021, 218
[6]   Stereocontrolled Construction of the 3,4-Dihydrothiacarbazol-2(9H)-one Skeleton by Using Bifunctional Squaramide-Catalyzed Cascade Reactions [J].
Chen, Shanren ;
Pan, Jianping ;
Wang, Youming ;
Zhou, Zhenghong .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (35) :7940-7947
[7]   Asymmetric Construction of Spiro[thiopyranoindole-benzoisothiazole] Scaffold via a Formal [3+3] Spiroannulation [J].
Chen, Xiang ;
Zhang, Jun-Qi ;
Yin, Shao-Jie ;
Li, Hai-Yan ;
Zhou, Wei-Qun ;
Wang, Xing-Wang .
ORGANIC LETTERS, 2015, 17 (17) :4188-4191
[8]   Enantioselective Construction of Functionalized Thiopyrano-lndole Annulated Heterocycles via a Formal Thio [3+31-Cyclization [J].
Chen, Xiang ;
Qi, Zheng-Hang ;
Zhang, Shao-Yun ;
Kong, Ling-Pei ;
Wang, Yong ;
Wang, Xing-Wang .
ORGANIC LETTERS, 2015, 17 (01) :42-45
[9]  
Chen Z.C., 2019, Angew. Chem, V131, P15163, DOI DOI 10.1002/ANGE.201907797
[10]   Transformations of Modified Morita-Baylis-Hillman Adducts from Isatins Catalyzed by Lewis Bases [J].
Chen, Zhi-Chao ;
Chen, Zhi ;
Du, Wei ;
Chen, Ying-Chun .
CHEMICAL RECORD, 2020, 20 (06) :541-555