Ruthenium complex catalyzed N-heterocyclization. Syntheses of N-substituted piperidines, morpholines, and piperazines from amines and 1, 5-diols
…, KT Huh, Y Ohsugi, Y Watanabe
Index: Tsuji, Yasushi; Huh, Keun-Tae; Ohsugi, Yukihiro; Watanabe, Yoshihisa Journal of Organic Chemistry, 1985 , vol. 50, # 9 p. 1365 - 1370
Full Text: HTML
Citation Number: 105
Abstract
1, 5-Pentanediol reacts with aliphatic and aromatic primary amines in the presence of a ruthenium catalyst modified with phosphine ligands to give N-substituted piperidines in fair to goods yields. The reactions were carried out at 15C-180" C for 5 h in dioxane. The nature of the phosphorus ligands has a remarkable effect on the catalytic activity. For the reaction of aromatic amines, triphenylphosphine is effective, while for aliphatic amines more basic ...
Related Articles:
[Wichitnithad, Wisut; O'Callaghan, James P.; Miller, Diane B.; Train, Brian C.; Callery, Patrick S. Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 24 p. 7482 - 7492]
An efficient palladium-catalyzed N-alkylation of amines using primary and secondary alcohols
[Dang, Tuan Thanh; Ramalingam, Balamurugan; Shan, Siah Pei; Seayad, Abdul Majeed ACS Catalysis, 2013 , vol. 3, # 11 p. 2536 - 2540]
[Otsuka, Maiko; Yokoyama, Hiroya; Endo, Kohei; Shibata, Takanori Organic and Biomolecular Chemistry, 2012 , vol. 10, # 19 p. 3815 - 3818]
[Sundberg, Richard J.; Walters, Claudia Powers; Bloom, Jonathan D. Journal of Organic Chemistry, 1981 , vol. 46, # 18 p. 3730 - 3732]
A convenient method for the selective reduction of amides to amines
[Raucher, Stanley; Klein, Peter Tetrahedron Letters, 1980 , vol. 21, p. 4061 - 4064]