Microwave-Assisted Metal-Free Synthesis of 2,8-Diaryl-6-aminoimidazo[1,2-a]pyridine via Amine-Triggered Benzannulation

被引:22
作者
Nagaraj, Muthupandi [1 ]
Boominathan, Muthusamy [1 ]
Muthusubramanian, Shanmugam [1 ]
Bhuvanesh, Nattamai [2 ]
机构
[1] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai 625021, Tamil Nadu, India
[2] Texas A&M Univ, Xray Diffract Lab, Dept Chem, College Stn, TX 77842 USA
关键词
alkynes; amination; annulation; fused ring systems; heterocycles; green chemistry; ONE-POT SYNTHESIS; BETA-KETO-ESTERS; CARBENE COMPLEXES; DERIVATIVES; INHIBITORS; CYCLIZATION; ANNULATION; BINDING; FACILE; AGENTS;
D O I
10.1055/s-0031-1290979
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient microwave-assisted metal-free amino benzannulation of aryl(4-aryl-1-(prop-2-ynyl)-1H-imidazol-2-yl) methanone with dialkylamines afforded a variety of 2,8-diaryl-6-aminoimidazo[1,2-a]pyridine in moderate to excellent yield.
引用
收藏
页码:1353 / 1357
页数:5
相关论文
共 46 条
[1]   TiCl4/t-BuNH2-promoted hydroamination/annulation of δ-keto-acetylenes:: Synthesis of novel pyrrolo[1,2-a]indol-2-carbaldehydes [J].
Abbiati, Giorgio ;
Casoni, Alessandro ;
Canevari, Valentina ;
Nava, Donatella ;
Rossi, Elisabetta .
ORGANIC LETTERS, 2006, 8 (21) :4839-4842
[2]   Microwave-Assisted, One-Pot Reaction of Pyridines, α-Bromoketones and Ammonium Acetate: An Efficient and Simple Synthesis of Imidazo[1,2-a]-pyridines [J].
Adib, Mehdi ;
Mohamadi, Ali ;
Sheikhi, Ehsan ;
Ansari, Samira ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2010, (11) :1606-1608
[3]   Tandem [8+2] Cycloaddition-[2+6+2] Dehydrogenation Reactions Involving Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines [J].
Aginagalde, Maialen ;
Vara, Yosu ;
Arrieta, Ana ;
Zangi, Ronen ;
Cebolla, Vicente L. ;
Delgado-Camon, Arantzazu ;
Cossio, Fernando P. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09) :2776-2784
[4]   Facile and versatile annulation of the imidazole ring:: Single and sequential cyclization reactions of Fischer carbene complexes with 1,4-diazafulvenes [J].
Barluenga, J ;
García-Rodríguez, J ;
Martínez, S ;
Suárez-Sobrino, AL ;
Tomás, M .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (12) :3201-3210
[5]   Synthetic approach to imidazo[1,2-a]pyridine derivatives by the intramolecular nitrone cycloaddition methodology [J].
Basso, D ;
Broggini, G ;
Passarella, D ;
Pilati, T ;
Terraneo, A ;
Zecchi, G .
TETRAHEDRON, 2002, 58 (22) :4445-4450
[6]   Synthesis of fused imidazo-pyridine and -azepine derivatives by sequential van Leusen/Heck reactions [J].
Beebe, X ;
Gracias, V ;
Djuric, SW .
TETRAHEDRON LETTERS, 2006, 47 (19) :3225-3228
[7]   An efficient and simple aminobenzannulation reaction: Pyrrolidine as a trigger for the synthesis of 1-amino-acridines [J].
Belmont, P ;
Belhadj, T .
ORGANIC LETTERS, 2005, 7 (09) :1793-1795
[8]   Synthesis of indeno-fused derivatives of quinolizinium salts, imidazo[1,2-a]pyridine, pyrido[1,2-a]indole, and 4H-quinolizin-4-one via benzannulated enyne-allenes [J].
Dai, WX ;
Petersen, JL ;
Wang, KK .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :6647-6652
[9]   CARDIOTONIC AGENTS .1. NOVEL 8-ARYL-SUBSTITUTED IMIDAZO[1,2-A] AND [1,5-A]PYRIDINES AND IMIDAZO[1,5-A]PYRIDINONES AS POTENTIAL POSITIVE INOTROPIC AGENTS [J].
DAVEY, D ;
ERHARDT, PW ;
LUMMA, WC ;
WIGGINS, J ;
SULLIVAN, M ;
PANG, D ;
CANTOR, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (08) :1337-1342
[10]   Rapid synthesis of 3-amino-imidazopyridines by a microwave-assisted four-component coupling in one pot [J].
DiMauro, Erin F. ;
Kennedy, Joseph M. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (03) :1013-1016