A facile and efficient method for the synthesis of N-substituted isoindolin-1-one derivatives under Pd(OAc)2/HCOOH system

作者: Yang Zhou , Ping Chen , Xue Lv , Junxing Niu , Yingying Wang

DOI: 10.1016/J.TETLET.2017.04.073

关键词:

摘要: A facile and efficient method for the synthesis of N-substituted isoindolin-1-one derivatives from 2-formylbenzoic acid amine under Pd(OAc)2/HCOOH system has been described. The whole process is carried out in ligand-free conditions furnished desired products by reductive intramolecular cyclization. Furthermore, this procedure applied successfully modification natural products, such as vindoline estrone.

参考文章(35)
Marriott Jb, Guckian M, Dalgleish Ag, Cookson S, Stirling D, Goodbourn S, Westby M, Shire Mg, Muller G, CC-3052: a water-soluble analog of thalidomide and potent inhibitor of activation-induced TNF-alpha production. Journal of Immunology. ,vol. 161, pp. 4236- 4243 ,(1998)
Diána Marosvölgyi-Haskó, Attila Takács, Zsuzsanna Riedl, László Kollár, High-yielding synthesis of 1-isoindolinone derivatives via palladium-catalysed cycloaminocarbonylation Tetrahedron. ,vol. 67, pp. 1036- 1040 ,(2011) , 10.1016/J.TET.2010.11.099
Masaharu Uno, Hyun Seung Ban, Hiroyuki Nakamura, 1-[4-(N-Benzylamino)phenyl]-3-phenylurea derivatives as a new class of hypoxia-inducible factor-1α inhibitors Bioorganic & Medicinal Chemistry Letters. ,vol. 19, pp. 3166- 3169 ,(2009) , 10.1016/J.BMCL.2009.04.122
Mark H. Norman, Douglas J. Minick, Greg C. Rigdon, Effect of Linking Bridge Modifications on the Antipsychotic Profile of Some Phthalimide and Isoindolinone Derivatives Journal of Medicinal Chemistry. ,vol. 39, pp. 149- 157 ,(1996) , 10.1021/JM9502201
Hasrat Ali, Johan E. van Lier, Reaction of benzeneselenenyl halides with estrogens Journal of The Chemical Society-perkin Transactions 1. pp. 269- 271 ,(1991) , 10.1039/P19910000269
Gábor Blaskó, Daniella J. Gula, Maurice Shamma, The Phthalideisoquinoline Alkaloids Journal of Natural Products. ,vol. 45, pp. 105- 122 ,(1982) , 10.1021/NP50020A001
Vishal Kumar, Upendra Sharma, Bikram Singh, Neeraj Kumar, Direct One-Pot Cobalt(II) Phthalocyanine Catalyzed Synthesis of N-Substituted Isoindolinones Australian Journal of Chemistry. ,vol. 65, pp. 1594- 1598 ,(2012) , 10.1071/CH12321
Jaco C. Breytenbach, Sandra van Dyk, Ilse van den Heever, Steven M. Allin, Claire C. Hodkinson, Christopher J. Northfield, Micheal I. Page, Synthesis and antimicrobial activity of some isoindolin-1-ones derivatives. Bioorganic & Medicinal Chemistry Letters. ,vol. 10, pp. 1629- 1631 ,(2000) , 10.1016/S0960-894X(00)00306-1
S. Fazal Hussain, Robert D. Minard, Alan J. Freyer, Maurice Shamma, New Alkaloids From Fumaria parviflora Journal of Natural Products. ,vol. 44, pp. 169- 178 ,(1981) , 10.1021/NP50014A005