Catalyst-Controlled Regioselective Approach to 1-Aminoisoquinolines and/or 1-Aminoisoindolines through Aminative Domino Cyclization of 2-Alkynylbenzonitriles
作者： Virsinha Reddy , Abhijeet S. Jadhav , Ramasamy Vijaya Anand
关键词:
摘要: A metal-catalyzed regioselective approach towards the synthesis of 1-aminoisoquinolines and/or 1-aminoisindolines through aminative domino cyclization 2-alkynylbenzonitriles with secondary amines has been developed under solvent-free conditions. It was found that regioselectivity reaction greatly influenced by choice metal catalyst. Copper-based catalysts favored 6-endo-dig leading to 1-aminoisoquinolines, whereas other such as triflates Zn, Ag, Bi, Sc and Yb formation 1-aminoisoindolines 5-exo-dig cyclization.
sci-hub.se 参考文章(68)
Virsinha Reddy, Abhijeet S. Jadhav, Ramasamy Vijaya Anand, A room-temperature protocol to access isoquinolines through Ag(i) catalysed annulation of o-(1-alkynyl)arylaldehydes and ketones with NH4OAc: elaboration to berberine and palmatine Organic & Biomolecular Chemistry. ,vol. 13, pp. 3732- 3741 ,(2015) , 10.1039/C4OB02641A
Bharat Lagu, Dake Tian, Dhanapalan Nagarathnam, Mohammad R. Marzabadi, Wai C. Wong, Shou W. Miao, Fengqi Zhang, Wanying Sun, George Chiu, James Fang, Carlos Forray, Raymond S. L. Chang, Richard W. Ransom, Tsing B. Chen, Stacey O'Malley, Kanyin Zhang, Kamlesh P. Vyas, Charles Gluchowski, Design and Synthesis of Novel α1a Adrenoceptor-Selective Antagonists. 3. Approaches To Eliminate Opioid Agonist Metabolites by Using Substituted Phenylpiperazine Side Chains Journal of Medicinal Chemistry. ,vol. 42, pp. 4794- 4803 ,(1999) , 10.1021/JM990202+
Karuppusamy Sakthivel, Kannupal Srinivasan, Synthesis of Naphthalene Amino Esters by the Blaise Reaction of o-Alkynylarenenitriles Journal of Organic Chemistry. ,vol. 79, pp. 3244- 3248 ,(2014) , 10.1021/JO500137M
Nuha Alharbi, Alejandro Díaz-Moscoso, Graham J. Tizzard, Simon J. Coles, Michael J. Cook, Andrew N. Cammidge, Improved syntheses of meso-aryl tetrabenzotriazaporphyrins (TBTAPs) Tetrahedron. ,vol. 70, pp. 7370- 7379 ,(2014) , 10.1016/J.TET.2014.06.086
Adrian L. Smith, Frenel F. DeMorin, Nick A. Paras, Qi Huang, Jeffrey K. Petkus, Elizabeth M. Doherty, Thomas Nixey, Joseph L. Kim, Douglas A. Whittington, Linda F. Epstein, Matthew R. Lee, Mark J. Rose, Carol Babij, Manory Fernando, Kristen Hess, Quynh Le, Pedro Beltran, Josette Carnahan, Selective Inhibitors of the Mutant B-Raf Pathway: Discovery of a Potent and Orally Bioavailable Aminoisoquinoline Journal of Medicinal Chemistry. ,vol. 52, pp. 6189- 6192 ,(2009) , 10.1021/JM901081G
Shengqing Ye, Huanhuan Wang, Jie Wu, 1-(isoquinolin-1-yl)urea library generation via three-component reaction of 2-alkynylbenzaldoxime, carbodiimide, with electrophile. ACS Combinatorial Science. ,vol. 13, pp. 120- 125 ,(2011) , 10.1021/CO100026Y
Brian K. Lee, Mark R. Biscoe, Stephen L. Buchwald, Simple, efficient protocols for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine Tetrahedron Letters. ,vol. 50, pp. 3672- 3674 ,(2009) , 10.1016/J.TETLET.2009.03.137
Simon Doherty, Julian G. Knight, John P. McGrady, Alexandra M. Ferguson, Nicholas A. B. Ward, Ross W. Harrington, William Clegg, ortho,ortho' -Substituted KITPHOS Monophosphines: Highly Efficient Ligands for Palladium-Catalyzed C‒C and C‒N Bond Formation Advanced Synthesis & Catalysis. ,vol. 352, pp. 201- 211 ,(2010) , 10.1002/ADSC.200900577
Santos Fustero, Maria Dolores Díaz, Juan Server Carrió, Enrique Aguilar, C−C versus C−N Annulation Reactions of 2‐Alkyl‐2‐oxazolines and 2‐Alkyl‐2‐thiazolines: A Simple Synthesis of Novel 3‐Aminoindene, Phthalimidine, Pyrrolidine, and Piperidine Derivatives European Journal of Organic Chemistry. ,vol. 2001, pp. 1195- 1201 ,(2001) , 10.1002/1099-0690(200103)2001:6<1195::AID-EJOC1195>3.0.CO;2-2
Y.M. Choi-Sledeski, M.R. Becker, D.M. Green, R. Davis, W.R. Ewing, H.J. Mason, C. Ly, A. Spada, G. Liang, D. Cheney, J. Barton, V. Chu, K. Brown, D. Colussi, R. Bentley, R. Leadley, C. Dunwiddie, H.W. Pauls, Aminoisoquinolines: Design and synthesis of an orally active benzamidine isostere for the inhibition of factor XA Bioorganic & Medicinal Chemistry Letters. ,vol. 9, pp. 2539- 2544 ,(1999) , 10.1016/S0960-894X(99)00421-7