Copper-catalyzed oxidative cyclization of 2-(1H-pyrrol-1-yl)aniline and alkylsilyl peroxides: a route to pyrrolo[1,2-a]quinoxalines

被引:4
作者
An, Zhenyu [1 ]
Miao, Man [1 ]
Sun, Fengkai [1 ]
Lan, Xiao-Bing [1 ]
Yu, Jian-Qiang [1 ]
Guo, Xiaoli [1 ]
Zhang, Jian [1 ,2 ]
机构
[1] Ningxia Med Univ, Coll Pharm, Key Lab Protect Dev & Utilizat Med Resources Liupa, Yinchuan, Ningxia Hui Aut, Peoples R China
[2] Shanghai Jiao Tong Univ, Sch Med, Med Chem & Bioinformat Ctr, Shanghai, Peoples R China
基金
中国国家自然科学基金; 国家重点研发计划;
关键词
EFFICIENT SYNTHESIS; C-C; ACID;
D O I
10.1039/d3ob01934a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method was developed for the one-pot construction of pyrrolo[1,2-a]quinoxalines via a Cu(ii)-catalyzed domino reaction between 2-(1H-pyrrol-1-yl)anilines and alkylsilyl peroxides. This reaction proceeds through C-C bond cleavage and new C-C and C-N bond formation. A mechanistic study suggests that alkyl radical species participate in the cascade reaction.
引用
收藏
页码:2370 / 2374
页数:5
相关论文
共 15 条
[1]  
Alleca Sergio, 2003, Farmaco (Lausanne), V58, P639
[2]   Synthesis, antimalarial activity, and molecular modeling of new pyrrolo[1,2-a]quinoxalines, bispyrrolo[1,2-a]quinoxalines, bispyrido[3,2-e]pyrrolo[1,2-a]pyrazines, and bispyrrolo[1,2-a]thieno[3,2-e]pyrazines [J].
Guillon, J ;
Grellier, P ;
Labaied, M ;
Sonnet, P ;
Léger, JM ;
Déprez-Poulain, R ;
Forfar-Bares, I ;
Dallemagne, P ;
Lemaître, N ;
Péhourcq, F ;
Rochette, J ;
Sergheraert, C ;
Jarry, C .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (08) :1997-2009
[3]   Synthesis of new pyrrolo[1,2-a]quinoxalines:: potential non-peptide glucagon receptor antagonists [J].
Guillon, J ;
Dallemagne, P ;
Pfeiffer, B ;
Renard, P ;
Manechez, D ;
Kervran, A ;
Rault, S .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1998, 33 (04) :293-308
[4]   Synthesis and biological evaluation of novel substituted pyrrolo[1,2-a]quinoxaline derivatives as inhibitors of the human protein kinase CK2 [J].
Guillon, Jean ;
Le Borgne, Marc ;
Rimbault, Charlotte ;
Moreau, Stephane ;
Savrimoutou, Solene ;
Pinaud, Noel ;
Baratin, Sophie ;
Marchivie, Mathieu ;
Roche, Severine ;
Bollacke, Andre ;
Pecci, Adali ;
Alvarez, Lautaro ;
Desplat, Vanessa ;
Jose, Joachim .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 65 :205-222
[5]   An Efficient Synthesis of Pyrrolo[1,2-a]quinoxalines by CopperCatalyzed C-H Activation of Arylacetic Acids [J].
Lade, Jatin J. ;
Patil, Bhausaheb N. ;
Vhatkar, Mahendra V. ;
Vadagaonkar, Kamlesh S. ;
Chaskar, Atul C. .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (11) :1579-1583
[6]   A Green Aerobic Oxidative Synthesis of Pyrrolo[1,2-a]quinoxalines from Simple Alcohols without Metals and Additives [J].
Li, Jixing ;
Zhang, Jinlong ;
Yang, Huameng ;
Gao, Zeng ;
Jiang, Gaoxi .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (01) :765-769
[7]   KI-Mediated One-Pot Transition-Metal-Rree Synthesis of 4-Phenylpyrrolo[1,2-a]quinoxalines [J].
Li, Shichen ;
Xie, Caixia ;
Chu, Xianglong ;
Dai, Zhen ;
Feng, Lei ;
Ma, Chen .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (31) :4950-4956
[8]   Application of α-amino acids for the transition-metal-free synthesis of pyrrolo[1,2-a]quinoxalines [J].
Liu, Huanhuan ;
Zhou, Feiyu ;
Luo, Wen ;
Chen, Yuxin ;
Zhang, Chenyang ;
Ma, Chen .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (34) :7157-7164
[9]   Bifunctional acidic ionic liquid-catalyzed decarboxylative cascade synthesis of quinoxalines in water under ambient conditions [J].
Liu, Shanshan ;
Zhang, Pingjun ;
Zhang, Yuanyuan ;
Zhou, Xianying ;
Liang, Jiahui ;
Nan, Jiang ;
Ma, Yangmin .
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (20) :5858-5865
[10]   Simple and Highly Efficient Synthesis of Indolo- and Pyrrolo[1,2-α]quinoxalines Promoted by Molecular Iodine [J].
Ramamohan, Mekala ;
Sridhar, Regati ;
Raghavendrarao, Kamaraju ;
Paradesi, Naidu ;
Chandrasekhar, Kothapally Bannoth ;
Jayaprakash, Sarva .
SYNLETT, 2015, 26 (08) :1096-1100