Diversity-oriented approach to spirocycles with indole moiety via Fischer indole cyclization, olefin metathesis and Suzuki-Miyaura cross-coupling reactions

被引：34

作者：

Kotha, Sambasivarao ^{[1
]}

Ali, Rashid ^{[1
]}

Srinivas, Venu ^{[1
]}

Krishna, Nimita G. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

TETRAHEDRON | 2015年 / 71卷 / 01期

关键词：

Spirocycles; Claisen rearrangement; Fischer indole cyclization; Ring-closing metathesis; Suzuki Miyaura cross-coupling; RING-CLOSING METATHESIS; CLAISEN REARRANGEMENT; NATURAL-PRODUCTS; ARYLBORONIC ACIDS; ONE-POT; ALKALOIDS; CATALYSTS; ROUTE; SPIRO; FUNCTIONALIZATION;

D O I：

10.1016/j.tet.2014.11.024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of aryl substituted spirocycles containing the indole moiety have been assembled through Claisen rearrangement, Fischer indole cyclization, ring-closing metathesis and the Suzuki-Miyaura cross-coupling reactions. Some of these molecules contain either a spirocyclic system or an indeno[1,2-b] indole framework, which is present in diverse bioactive targets. Here, we have used simple and readily available starting materials to generate a library of spirocycles with an indole unit in their structures. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：129 / 138

页数：10

共 22 条

[1] Diversity-Oriented Approach to Macrocyclic Cyclophane Derivatives by Suzuki-Miyaura Cross-Coupling and Olefin Metathesis as Key Steps
Kotha, Sambasivarao
Chavan, Arjun S.
Shaikh, Mobin
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01) : 482 - 489
[2] A simple approach to bis-spirocycles and spiroindole derivatives via green methods such as Fischer indolization, ring-closing metathesis, and Suzuki-Miyaura cross-coupling
Kotha, Sambasivarao
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TURKISH JOURNAL OF CHEMISTRY, 2015, 39 (06) : 1190 - 1198
[3] Diversity-Oriented Synthesis of Biaryl Derivatives Using Cross-Enyne Metathesis, Diels-Alder Reaction, and Suzuki-Miyaura Cross-Coupling as Key Steps
Kotha, Sambasivarao
Seema, Vittal
SYNLETT, 2011, (16) : 2329 - 2334
[4] DIVERSITY ORIENTED APPROACH TO 9-ARYL-SUBSTITUTED NAPHTHOXEPINE DERIVATIVES VIA CLAISEN REARRANGEMENT, RING-CLOSING METATHESIS AND SUZUKI-MIYAURA CROSS-COUPLING AS KEY STEPS
Kotha, Sambasivarao
Srinivas, Venu
Krishna, Nimita G.
HETEROCYCLES, 2012, 86 (02) : 1555 - 1563
[5] Formation of arenes via diallylarenes:: Strategic utilization of Suzuki-Miyaura cross-coupling, Claisen rearrangement and ring-closing metathesis
Kotha, Sambasivarao
Shah, Vrajesh R.
Mandal, Kalyaneswar
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (07) : 1159 - 1172
[6] A diversity-oriented approach to indolocarbazoles via Fischer indolization and olefin metathesis: total synthesis of tjipanazole D and I
Kotha, Sambasivarao
Saifuddin, Mohammad
Aswar, Vikas R.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (41) : 9868 - 9873
[7] Synthesis of Angucycline/Tetrangulol Derivatives Using Suzuki-Miyaura Cross-Coupling and Ring-Closing Carbonyl-Olefin Metathesis Reactions
Jagot, Fatema
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Ngwira, Kennedy J.
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de Koning, Charles B.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (24)
[8] Applications of α-Phosphonovinyl Tosylates in the Synthesis of α-Arylethenylphosphonates via Suzuki-Miyaura Cross-Coupling Reactions
Fang, Yewen
Zhang, Li
Li, Jinjian
Jin, Xiaoping
Yuan, Meijuan
Li, Ruifeng
Wu, Rong
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ORGANIC LETTERS, 2015, 17 (04) : 798 - 801
[9] Diversity-oriented approach to natural product inspired pyrano-carbazole derivatives: strategic utilization of hetero-Diels-Alder reaction, Fischer indolization and the Suzuki-Miyaura cross-coupling reaction
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Ali, Rashid
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TETRAHEDRON, 2015, 71 (47) : 9003 - 9011
[10] New synthetic approach to a [1.1.6] metapara cyclophane derivative via Suzuki-Miyaura cross-coupling and ring-closing metathesis
Kotha, S
Mandal, K
Arora, KK
Pedireddi, R
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (09) : 1215 - 1218

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