Iron-catalyzed unprecedented formation of benzo[d]imidazo[2,1-b]thiazoles under solvent-free conditions

被引:39
作者
Balwe, Sandip Gangadhar [1 ]
Jeong, Yeon Tae [1 ]
机构
[1] Pukyong Natl Univ, Dept Image Sci & Engn, Busan 608737, South Korea
关键词
MULTICOMPONENT REACTIONS; BIOLOGICAL EVALUATION; CYCLIC SULFONAMIDES; NITROALKANES; CYCLIZATION; DISCOVERY; DESIGN; POTENT; PET;
D O I
10.1039/c6ra24183b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The unprecedented formation of benzo[d]imidazo[2,1-b]thiazole during iron-catalyzed coupling of 2-aminobenzothiazole, aldehydes with nitroalkane in air has been observed. This unique transformation possibly occurs through a sequential aza-Henry reaction and subsequent intramolecular cyclization, followed by denitration. A variety of substituted benzo[d]imidazo[2,1-b]thiazole are obtained using this protocol.
引用
收藏
页码:107225 / 107232
页数:8
相关论文
共 57 条
[31]   PREPARATION OF 6-MEMBERED, 7-MEMBERED AND 8-MEMBERED SULTAMS BY FRIEDEL-CRAFTS CYCLIZATION OF OMEGA-PHENYLALKANESULFAMOYL CHLORIDES [J].
KATRITZKY, AR ;
WU, J ;
RACHWAL, S ;
RACHWAL, B ;
MACOMBER, DW ;
SMITH, TP .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1992, 24 (04) :463-467
[32]  
Kumbhar V. V., 2013, PHARM CHEM, V5, P274
[33]   Synthesis and biological evaluation of novel Mannich bases of 2-arylimidazo[2,1-b]benzothiazoles as potential anti-cancer agents [J].
Kumbhare, Ravindra M. ;
Kumar, K. Vijay ;
Ramaiah, M. Janaki ;
Dadmal, Tulshiram ;
Pushpavalli, S. N. C. V. L. ;
Mukhopadhyay, Debasmita ;
Divya, B. ;
Devi, T. Anjana ;
Kosurkar, Umesh ;
Pal-Bhadra, Manika .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) :4258-4266
[34]  
Loupy A, 1999, TOP CURR CHEM, V206, P153
[35]   Iron(III)-Catalyzed Four-Component Coupling Reaction of 1,3-Dicarbonyl Compounds, Amines, Aldehydes, and Nitroalkanes: A Simple and Direct Synthesis of Functionalized Pyrroles [J].
Maiti, Sukhendu ;
Biswas, Srijit ;
Jana, Umasish .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) :1674-1683
[36]   Synthesis of phosphorus and sulfur heterocycles via ring-closing olefin metathesis [J].
McReynolds, MD ;
Dougherty, JM ;
Hanson, PR .
CHEMICAL REVIEWS, 2004, 104 (05) :2239-2258
[37]   FeCl3/ZnI2-Catalyzed Synthesis of Benzo[d]imidazo[2,1-b]thiazole through Aerobic Oxidative Cyclization between 2-Aminobenzothiazole and Ketone [J].
Mishra, Subhajit ;
Monir, Kamarul ;
Mitra, Shubhanjan ;
Hajra, Alakananda .
ORGANIC LETTERS, 2014, 16 (23) :6084-6087
[38]  
Namboothiri INN, 2008, TOP HETEROCYCL CHEM, V12, P1, DOI 10.1007/7081_2007_101
[39]   Nitro-Mannich Reaction [J].
Noble, Adam ;
Anderson, James C. .
CHEMICAL REVIEWS, 2013, 113 (05) :2887-2939
[40]   Synthesis and Antibacterial Activity of a Novel Series of 2,3-Diaryl-substituted-imidazo(2,1-b)-benzothiazole Derivatives [J].
Palkar, Mahesh ;
Noolvi, Malleshappa ;
Sankangoud, Ramappa ;
Maddi, Veeresh ;
Gadad, Andanappa ;
Nargund, Laxmi Venkat G. .
ARCHIV DER PHARMAZIE, 2010, 343 (06) :353-359