New and Efficient Synthesis of 2,3,4-Trisubstituted 2H-Pyrrolo[3,4-c]quinolines via a MCR/Staudinger/Aza-Wittig Sequence

被引:15
作者
Qu, Feng [1 ]
Hu, Ruo-Fei [1 ]
Gao, Le [1 ]
Wu, Jing [1 ]
Cheng, Xiao-Hong [2 ]
Wang, Song [2 ]
He, Ping [1 ,2 ]
机构
[1] Hubei Univ Arts & Sci, Coll Chem Engn & Food Sci, Xiangyang 441053, Hubei Province, Peoples R China
[2] Hubei Univ Arts & Sci, Hubei Key Lab Low Dimens Optoelect Mat & Devices, Xiangyang 441053, Hubei Province, Peoples R China
来源
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 23期
基金
中国国家自然科学基金;
关键词
2H-pyrrolo[3; 4-c]quinolones; multicomponent reaction; azide; aza-Wittig reaction; iminophosphorane; HIGHLY SUBSTITUTED PYRROLES; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; FUNCTIONALIZED PYRROLES; 4-COMPONENT SYNTHESIS; DERIVATIVES; AMINES;
D O I
10.1055/s-0035-1560208
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and efficient method for the construction of 2,3,4-trisubstituted 2H-pyrrolo[3,4-c]quinoline derivatives was developed. Starting from easily accessible 2-azidobenzaldehyde, nitromethane, 1,3-dicarbonyl compounds, and various amines gave the multicomponent reaction (MCR) products, 1-substituted 3-acyl-4-(2-azidophenyl)-2-methyl-1H-pyrroles, that underwent Staudinger/aza-Wittig cyclization of in the presence of triphenylphosphine to give the final products.
引用
收藏
页码:3701 / 3710
页数:10
相关论文
共 54 条
[1]   A reinvestigation of the structure of the erythro and xanthoapocyanine dyes: Some unusual aspects of quinoline chemistry [J].
Afarinkia, K ;
Ansari, MR ;
Bird, CW ;
Gyambibi, I .
TETRAHEDRON LETTERS, 1996, 37 (27) :4801-4804
[2]   Synthesis of 3-oxo-1,4-diazepine-5-carboxamides and 6-(4-oxo-chromen-3-yl)-pyrazinones via sequential Ugi 4CC/Staudinger/intramolecular nucleophilic cyclization and Ugi 4CC/Staudinger/aza-Wittig reactions [J].
Akbarzadeh, Roya ;
Our, Tayebeh Amanp ;
Bazgir, Ayoob .
TETRAHEDRON, 2014, 70 (43) :8142-8147
[3]   Synthesis of 4-Acetoxyindoles and Related Derivatives by Means of Air Oxidation of 4-Oxo-4,5,6,7-tetrahydroindoles Obtained from Nitroalkenes and Cyclohexane-1,3-diones [J].
Arai, Masaki ;
Miyauchi, Yayoi ;
Miyahara, Tadashi ;
Ishikawa, Teruhiko ;
Saito, Seiki .
SYNLETT, 2009, (01) :122-126
[4]   Montmorillonite clay catalyzed synthesis of functionalized pyrroles through domino four-component coupling of amines, aldehydes, 1,3-dicarbonyl compounds and nitroalkanes [J].
Bharate, Jaideep B. ;
Sharma, Rajni ;
Aravinda, Subrayashastry ;
Gupta, Vivek K. ;
Singh, Baldev ;
Bharate, Sandip B. ;
Vishwakarma, Ram A. .
RSC ADVANCES, 2013, 3 (44) :21736-21742
[5]   Organic azides:: An exploding diversity of a unique class of compounds [J].
Bräse, S ;
Gil, C ;
Knepper, K ;
Zimmermann, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240
[6]   Higher-order multicomponent reactions: beyond four reactants [J].
Brauch, Sebastian ;
van Berkel, Sander S. ;
Westermann, Bernhard .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) :4948-4962
[7]   SOME N-SUBSTITUTED 2-AMINO QUINOLINE-3,4-DICARBOXIMIDES-AND 2-METHYLQUINOLINE-3,4-DICARBOXIMIDES [J].
CAMPAIGN.E ;
HUTCHINS.JH .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1970, 7 (03) :655-&
[8]   Synthesis of pseudopeptidic [(5H)-6-oxodibenzo[b,f][1,5]diazocine-5-yl]arylglycinamides by an Ugi 4CC/Staudinger/aza-Wittig sequence [J].
Corres, Nazaret ;
Delgado, Jacinto J. ;
Garcia-Valverde, Maria ;
Marcaccini, Stefano ;
Rodriguez, Teresa ;
Rojo, Josefa ;
Torroba, Tomas .
TETRAHEDRON, 2008, 64 (09) :2225-2232
[9]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[10]   Chemistry and Biology Of Multicomponent Reactions [J].
Domling, Alexander ;
Wang, Wei ;
Wang, Kan .
CHEMICAL REVIEWS, 2012, 112 (06) :3083-3135