Rh(III)-Catalyzed Chemoselective [4+2] Annulations for the Synthesis of [1,3]Oxazinoindolones: A Combined Experimental and Computational Study

被引：2
作者：
Kumar, Perla Bharath [1 ,2 ]
Raju, Chittala Emmaniel [1 ,2 ]
Roy, Saikat [3 ]
Anoop, Anakuthil [3 ]
Chandra, Rajesh [1 ,2 ]
Sridhar, Balasubramanian [2 ,4 ]
Karunakar, Galla V. [1 ,2 ]
机构：
[1] Indian Inst Chem Technol, Fluoro & Agrochem Div, CSIR, Hyderabad 500007, India
[2] Acad Sci & Innovat Res, Ghaziabad 201002, India
[3] Indian Inst Technol Kharagpur, Dept Chem, Kharagpur 721302, India
[4] Indian Inst Chem Technol, Ctr Xray Crystallog, CSIR, Hyderabad 500007, India
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 41期
关键词：
C-H BONDS; DIVERGENT SYNTHESIS; INDOLES; ALKYNES; ACCESS;
D O I：
10.1021/acs.orglett.4c02770
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The interaction of N-alkoxy-1H-indole-1-carboxamides with transition metals leads to indole-fused heterocyclic scaffolds through directing group leaving/migration, [3 + 2], N-C2 [4 + 1], and [4 + 2] annulations. However, the corresponding O-C2 [4 + 2] annulation reactions have never been reported. Herein, we report the chemoselective annulation of N-alkoxy-1H-indole-1-carboxamides catalyzed by Rh(III), affording [1,3]oxazinoindolones through a hitherto unknown reaction pathway. This unprecedented C2 oxygen cyclization, rather than the known C2 nitrogen cyclization to form oxazinoindolones via five key steps, has been explained using density functional theory.
引用
收藏
页码：8680 / 8685
页数：6
相关论文
共 47 条
[1]   Selective Synthesis of Fused Tricyclic [1,3]oxazino[3,4-a]indolone and Dihydropyrimido [1,6-a]indolone via Rh(III)-catalyzed [3+3] or [4+2] C-H Annulation [J].
Chen, Junyu ;
Zhong, Tianshuo ;
Zheng, Xiangyun ;
Yin, Chuanliu ;
Zhang, Lei ;
Zhou, Jian ;
Jiang, Xinpeng ;
Yu, Chuanming .
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (02) :446-452
[2]   Rh(iii)-catalyzed C-H activation/annulation of N-carbamoylindoles with CF3-imidoyl sulfoxonium ylides for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones [J].
Duan, Yubo ;
Lu, Shu-Ning ;
Yang, Zuguang ;
Chen, Zhengkai ;
Wu, Xiao-Feng .
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (15) :3843-3848
[3]   3d Transition Metals for C-H Activation [J].
Gandeepan, Parthasarathy ;
Mueller, Thomas ;
Zell, Daniel ;
Cera, Gianpiero ;
Warratz, Svenja ;
Ackermann, Lutz .
CHEMICAL REVIEWS, 2019, 119 (04) :2192-2452
[4]   Synthesis of Indole-Fused Oxepines via C-H Activation Initiated Diastereoselective [5+2] Annulation of Indoles with 1,6-Enynes [J].
Huang, Xiaoli ;
Shi, Yan ;
Wang, Yongzhuang ;
Jiao, Jiao ;
Tang, Yuhai ;
Li, Jing ;
Xu, Silong ;
Li, Yang .
ORGANIC LETTERS, 2021, 23 (21) :8365-8369
[5]   A Formal [5+1] Annulation Reaction of Sulfur Ylides and 2-(1H-indol-2-yl)phenols: Access to Indole-Fused 4H-benzo[e][1,3]oxazines [J].
Jia, Penghao ;
Huang, You .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (16) :3044-3048
[6]   Gold (I)-Promoted Intermolecular Cascade Annulation to Access 2-Hydroxybenzocarbazoles via a Meyer-Schuster Rearrangement [J].
Kadiyala, Veerabhushanam ;
Raju, Chittala Emmaniel ;
Bania, Kusum K. ;
Sridhar, Balasubramanian ;
Karunakar, Galla, V .
CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (03)
[7]   Gold-Catalyzed Synthesis of 6-Hydroxyindoles from Alkynylcyclohexadienones and Substituted Amines [J].
Kadiyala, Veerabhushanam ;
Kumar, Perla Bharath ;
Balasubramanian, Sridhar ;
Karunakar, Galla V. .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (18) :12228-12236
[8]   Formal SN-Type Reactions in Rhodium(III)-Catalyzed C-H Bond Activation [J].
Kuhl, Nadine ;
Schroeder, Nils ;
Glorius, Frank .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) :1443-1460
[9]   Propargylic Alcohols as Coupling Partners in Transition-Metal-Catalyzed Arene C-H Activation [J].
Kumar, Gadi Ranjith ;
Rajesh, Manda ;
Lin, Shuimu ;
Liu, Shouping .
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (23) :5238-5256
[10]   Gold(I)-Catalyzed Regioselective Cyclization to Access Cyclopropane-Fused Tetrahydrobenzochromenes [J].
Kumar, Perla Bharath ;
Raju, Chittala Emmaniel ;
Chandubhai, Patel Hinal ;
Sridhar, Balasubramanian ;
V. Karunakar, Galla .
ORGANIC LETTERS, 2022, :6761-6766
12345