Temperature-Dependent, Switchable Synthesis of α-Carbolines and Tetrahydropyrrolo[2,3-b]indoles via Formal [4+1+1] and [3+1+1] Cyclizations

被引：0
作者：
Xing, Siyang [1 ,2 ]
Jin, Lvrong [1 ,2 ]
Jing, Fangfang [1 ,2 ]
Wang, Xiqing [1 ,2 ]
Pang, Jingyu [1 ,2 ]
Zhu, Bolin [1 ,2 ]
机构：
[1] Tianjin Normal Univ, Tianjin Key Lab Struct & Performance Funct Mol, Tianjin 300387, Peoples R China
[2] Tianjin Normal Univ, Coll Chem, Tianjin 300387, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 23期
基金：
中国国家自然科学基金;
关键词：
ONE-POT SYNTHESIS; TRYPTAMINE DERIVATIVES; TRYPTOPHAN; TETRAHYDROPYRROLOINDOLES; ATHEROSCLEROSIS; IMPLITAPIDE; INHIBITOR; EFFICIENT; ROUTE;
D O I：
10.1021/acs.joc.5c00683
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A switchable one-pot, three-component cyclization of 3-vinylindoles, sulfonyl azides, and alpha-bromoketones has been developed for the synthesis of alpha-carbolines and tetrahydropyrrolo[2,3-b]indoles. The advantages of this strategy include excellent product selectivity, good functional group tolerance, highly functionalized products, and mild conditions.
引用
收藏
页码：7818 / 7831
页数：14
相关论文
共 52 条
[1]   Synthesis of 5,6-dihydroquinolines and succinates via the reaction of α,α-dicyanoolefins and acetylenic esters in a ratio of 2:1 [J].
Alizadeh, Abdolali ;
Hosseini, Seyed Yasub ;
Sedighian, Hadi ;
Bayat, Fahimeh ;
Zhu, Zhe ;
Dusek, Michal .
TETRAHEDRON, 2015, 71 (41) :7885-7891
[2]   SYNTHESIS AND POTENTIAL ANXIOLYTIC ACTIVITY OF 4-AMINO-PYRIDO[2,3-B]INDOLES [J].
BOLTON, D ;
FORBES, IT ;
HAYWARD, CJ ;
PIPER, DC ;
THOMAS, DR ;
THOMPSON, M ;
UPTON, N .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (10) :1941-1946
[3]   A synthetic strategy using Witkop's pyrroloindole for (-)-debromoflustramine B, (+)-ent-debromoflustramine B and (+)-ent-debromoflustramide B [J].
Cardoso, A. Sofia P. ;
Marques, M. Manuel B. ;
Srinivasan, Natarajan ;
Prabhakar, Sundaresan ;
Lobo, Ana M. .
TETRAHEDRON, 2007, 63 (41) :10211-10225
[4]   A solvent controlled regioselective synthesis of 2-and 4-substituted α-carbolines under palladium catalysis [J].
Chatterjee, Sarat ;
Khatun, Rousunara ;
Ali, Mahammad ;
Chowdhury, Chinmay .
CHEMICAL COMMUNICATIONS, 2024, 60 (58) :7427-7430
[5]   Copper-catalyzed cyclization of iodo-tryptophans:: A straightforward synthesis of pyrroloindoles [J].
Coste, Alexis ;
Toumi, Mathieu ;
Wright, Karen ;
Razafimahaleo, Vanessa ;
Couty, Francois ;
Marrot, Jerome ;
Evano, Gwilherm .
ORGANIC LETTERS, 2008, 10 (17) :3841-3844
[6]   Chemistry of the hexahydropyrrolo[2,3-b]indoles:: Configuration, conformation, reactivity, and applications in synthesis [J].
Crich, David ;
Banerjee, Abhisek .
ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (02) :151-161
[7]   Lewis-Base Dependent (3+3) Annulations of Acetoxy Allenoates with Iminoindolines: α-Carboline Scaffolds with Varied Substituents [J].
Debnath, Shubham ;
Kumar, A. Sanjeeva ;
Chauhan, Sachin ;
Swamy, K. C. Kumara .
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (24) :4316-4332
[8]   Total Synthesis of (+)-Chimonanthine, (+)-Folicanthine, and (-)-Calycanthine [J].
Ding, Ming ;
Liang, Kangjiang ;
Pan, Rui ;
Zhang, Hongbin ;
Xia, Chengfeng .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (20) :10309-10316
[9]  
Ding ZY, 2024, ORG LETT, V26, P5295, DOI 10.1021/acs.orglett.4c01631
[10]   Chemoselective three-component synthesis of α-carbolines under metal-free conditions [J].
Feng, Wei ;
Zhang, Chao ;
Zhou, Xinlin ;
You, Kuiyi ;
Deng, Guo-Jun ;
Chen, Shanping .
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (21) :5457-5462
123456