Benzannulation strategies for the synthesis of carbazoles, indolocarbazoles, benzocarbazoles, and carbolines

被引:78
作者
Banerjee, Ankush [1 ]
Kundu, Samrat [1 ]
Bhattacharyya, Arya [1 ]
Sahu, Samrat [1 ]
Maji, Modhu Sudan [1 ]
机构
[1] Indian Inst Technol Kharagpur, Dept Chem, Kharagpur 721302, W Bengal, India
关键词
ONE-POT SYNTHESIS; INDIUM-CATALYZED ANNULATION; DIELS-ALDER REACTION; C-H ACTIVATION; FACILE SYNTHESIS; FUNCTIONALIZED CARBAZOLES; SUBSTITUTED CARBAZOLES; GAMMA-CARBOLINES; BETA-CARBOLINES; RELAY CATALYSIS;
D O I
10.1039/d1qo00092f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nitrogen-containing pi-excessive aromatic heterocycles, in particular, carbazoles, indolocarbazoles, benzocarbazoles, and carbolines have been considered the fundamental backbone of organic chemistry for many decades due to their omnipresence in natural products, alkaloids, terpenes, marketed drugs, medicinally active compounds, organic materials, etc. Together with their ever-increasing importance, there has been a multi-dimensional significant advancement in the last decade towards their synthesis. This review presents an analysis of several exciting classical benzannulation and non-classical benzannulation approaches developed in the past decade (2010-2020) for the construction of carbazoles, indolocarbazoles, benzocarbazoles, and carbolines. The principal aim of this review is the detailed discussion of several fascinating mechanistic pathways together with the role of numerous key reagents and catalysts. Furthermore, the efficacy of these numerous benzannulation techniques towards the downstream synthesis of natural alkaloids, organic materials, and medicinally important scaffolds together with upcoming key challenges in this field are also covered in detail.
引用
收藏
页码:2710 / 2771
页数:62
相关论文
共 176 条
[1]   Access to Imidazo[1,2-a]pyridines via Annulation of α-Keto Vinyl Azides and 2-Aminopyridines [J].
Adiyala, Praveen Reddy ;
Mani, Geeta Sai ;
Nanubolu, Jagadeesh Babu ;
Shekar, Kunta Chandra ;
Maurya, Ram Awatar .
ORGANIC LETTERS, 2015, 17 (17) :4308-4311
[2]   Versatile Synthesis of Polyfunctionalized Carbazoles from (3-Iodoindol-2-yl)butynols via a Gold-Catalyzed Intramolecular Iodine-Transfer Reaction [J].
Alcaide, Benito ;
Almendros, Pedro ;
Alonso, Jose M. ;
Busto, Eduardo ;
Fernandez, Israel ;
Pilar Ruiz, M. ;
Xiaokaiti, Gulinigaer .
ACS CATALYSIS, 2015, 5 (06) :3417-3421
[3]   Palladium-Catalyzed Tandem Regioselective Oxidative Coupling from Indoles and Maleimides: One-Pot Synthesis of Indolopyrrolocarbazoles and Related Indolylmaleimides [J].
An, Yu-Long ;
Yang, Zhen-Hua ;
Zhang, He-Hui ;
Zhao, Sheng-Yin .
ORGANIC LETTERS, 2016, 18 (02) :152-155
[4]   Asymmetric Synthesis of Axially Chiral Benzocarbazole Derivatives Based on Catalytic Enantioselective Hydroarylation of Alkynes [J].
Arae, Sachie ;
Beppu, Shota ;
Kawatsu, Takahiro ;
Igawa, Kazunobu ;
Tomooka, Katsuhiko ;
Irie, Ryo .
ORGANIC LETTERS, 2018, 20 (16) :4796-4800
[5]   Diversity-Oriented Synthesis of Polycyclic Indoles: Bronsted or Lewis Acid Catalyzed Three-Component Reaction for the Synthesis of α-Carbolines and Pyrimidoindoles [J].
Arigela, Rajesh K. ;
Kumar, Ravi ;
Samala, Srinivas ;
Gupta, Sahaj ;
Kundu, Bijoy .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (27) :6057-6066
[6]   A Two-Step Synthesis of Unsymmetrical 1,4-Disubstituted Carbazoles from Sulfonylindoles Under Heterogeneous Catalysis [J].
Ballini, Roberto ;
Gabrielli, Serena ;
Palmieri, Alessandro ;
Petrini, Marino .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (14-15) :2459-2462
[7]   A Bronsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α-(3-Indolyl) Ketones by Using 2-Benzyloxy Aldehydes [J].
Banerjee, Ankush ;
Maji, Modhu Sudan .
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (49) :11521-11527
[8]   Formal [4+2] benzannulation of 2-alkenyl indoles with aldehydes: a route to structurally diverse carbazoles and bis-carbazoles [J].
Banerjee, Ankush ;
Guin, Avishek ;
Saha, Shuvendu ;
Mondal, Anushree ;
Maji, Modhu Sudan .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (07) :1822-1826
[9]   Benzannulation of 2-Alkenylindoles using Aldehydes by Sequential Triple-Relay Catalysis: A Route to Carbazoles and Carbazole Alkaloids [J].
Banerjee, Ankush ;
Sahu, Samrat ;
Maji, Modhu Sudan .
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (11) :1860-1866
[10]   Through-Space 1,4-Palladium Migration and 1,2-Aryl Shift: Direct Access to Dibenzo[a,c]carbazoles through a Triple C-H Functionalization Cascade [J].
Bhunia, Samir Kumar ;
Polley, Arghya ;
Natarajan, Ramalingam ;
Jana, Ranjan .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (47) :16786-16791