Metal-Free Ring Opening Cyclization of Cyclopropane Carbaldehydes and N-Benzyl Anilines: An Eco-Friendly Access to Functionalized Benzo[b]azepine Derivatives

被引:22
作者
Dey, Raghunath [1 ]
Banerjee, Prabal [1 ]
机构
[1] Indian Inst Technol Ropar, Dept Chem, Nangal Rd, Rupnagar 140001, Punjab, India
关键词
cyclopropane carbaldehyde; N-benzyl aniline; metal-free ring opening cyclization; benzo[b]azepine; DONOR-ACCEPTOR CYCLOPROPANES; SUBSTITUTED CYCLOPROPANE; 3+2 CYCLOADDITION; ACID; ALKYNES;
D O I
10.1002/adsc.201801714
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Herein, we report a p-toluenesulfonic acid (PTSA) initiated mild and user-friendly ring opening/domino ring opening cyclization reaction (depends on substituent present in N-benzyl aniline) of cyclopropane carbaldehyde and N-benzyl aniline towards the formation of substituted 4-amino butanal/2,3-dihydro-1H-benzo[b]azepine. The product dihydro-1H-benzo[b]azepine was also converted into the corresponding tetrahydro-1H-benzo[b]azepine.
引用
收藏
页码:2849 / 2854
页数:6
相关论文
共 36 条
[1]   SELECTIVE REDUCTION OF ALKENES AND ALKYNES BY REAGENT LITHIUM ALUMINUM HYDRIDE TRANSITION-METAL HALIDE [J].
ASHBY, EC ;
LIN, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (13) :2567-2572
[2]   Formal Insertion of Thioketenes into Donor-Acceptor Cyclopropanes by Lewis Acid Catalysis [J].
Augustin, Andre U. ;
Busse, Marius ;
Jones, Peter G. ;
Werz, Daniel B. .
ORGANIC LETTERS, 2018, 20 (03) :820-823
[3]   Application of p-toluenesulfonic Acid (PTSA) in Organic Synthesis [J].
Baghernejad, Bita .
CURRENT ORGANIC CHEMISTRY, 2011, 15 (17) :3091-3097
[4]  
Belal F, 2004, PROF DRUG SUB EXCIP, V31, P117
[5]   Ring Opening of Donor-Acceptor Cyclopropanes with N-Nucle-ophiles [J].
Budynina, Ekaterina M. ;
Ivanov, Konstantin L. ;
Sorokin, Ivan D. ;
Melnikov, Mikhail Ya. .
SYNTHESIS-STUTTGART, 2017, 49 (14) :3035-3068
[6]   Heterocycles from cyclopropanes: applications in natural product synthesis [J].
Carson, Cheryl A. ;
Kerr, Michael A. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3051-3060
[7]   (3+3)-Annulation of Donor-Acceptor Cyclopropanes with Diaziridines [J].
Chagarovskiy, Alexey O. ;
Vasin, Vladimir S. ;
Kuznetsov, Vladimir V. ;
Ivanova, Olga A. ;
Rybakov, Victor B. ;
Shumsky, Alexey N. ;
Makhova, Nina N. ;
Trushkov, Igor V. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (32) :10338-10342
[8]   Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2-b]pyridazines [J].
Dey, Raghunath ;
Kumar, Pankaj ;
Banerjeee, Prabal .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (10) :5438-5449
[9]   Lewis Acid Catalyzed Diastereoselective Cycloaddition Reactions of Donor Acceptor Cyclopropanes and Vinyl Azides: Synthesis of Functionalized Azidocyclopentane and Tetrahydropyridine Derivatives [J].
Dey, Raghunath ;
Banerjee, Prabal .
ORGANIC LETTERS, 2017, 19 (02) :304-307
[10]   The art of meeting palladium specifications in active pharmaceutical ingredients produced by Pd-catalyzed reactions [J].
Garrett, CE ;
Prasad, K .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (08) :889-900