130284-49-0Relevant articles and documents
Reductive one batch synthesis of N-substituted pyrrolidines from primary amines and 2,5-dimethoxytetrahydrofuran
Verardo, Giancarlo,Dolce, Anna,Toniutti, Nicoletta
, p. 74 - 79 (1999)
The construction of the pyrrolidine ring about a nitrogen of a primary amine by a reductive condensation reaction using 2,5- dimethoxytetrahydrofuran and sodium borohydride in acidic water medium is described. The reaction is fast, affords good to excellent yields and appears insensitive to electron effects and severe steric hindrance; it is found to be compatible with a large variety of aryl substituents, including nitro and oxo groups. The reaction allows the introduction of two deuterium atoms, with label conservation, in both the α-positions of the pyrrolidine ring by the use of sodium borodeuteride instead of sodium borohydride.
Phosphoryl chloride-mediated solvent-free synthesis of N-aryl-substituted azacycles from arylamines and cyclic ethers
Tran, Van Hieu,La, Minh Thanh,Kim, Hee-Kwon
supporting information, p. 1860 - 1863 (2019/06/19)
A solvent- and metal-free protocol for preparation of N-aryl substituted azacycles from arylamines and cyclic ethers is described. In this method, the combination of POCl3 and DBU is crucial for conversion of arylamines and cyclic ethers to five- and six-membered azacycles. Without solvent, a variety of N-aryl-substituted, five-membered azacycles (pyrrolidines, 2-methylpyrrolidines, and piperidine) and six-membered azacycles (isoindolines and tetrahydroisoquinolines) are synthesized in high yields. This green method provides a sustainable and efficient approach for the preparation of azacycles from various cyclic ethers.
Dual C(sp3)?H Bond Functionalization of N-Heterocycles through Sequential Visible-Light Photocatalyzed Dehydrogenation/[2+2] Cycloaddition Reactions
Xu, Guo-Qiang,Xu, Ji-Tao,Feng, Zhi-Tao,Liang, Hui,Wang, Zhu-Yin,Qin, Yong,Xu, Peng-Fei
supporting information, p. 5110 - 5114 (2018/03/27)
Herein we describe a mild method for the dual C(sp3)?H bond functionalization of saturated nitrogen-containing heterocycles through a sequential visible-light photocatalyzed dehydrogenation/[2+2] cycloaddition procedure. As a complementary approach to the well-established use of iminium ion and α-amino radical intermediates, the elusive cyclic enamine intermediates were effectively generated by photoredox catalysis under mild conditions and efficiently captured by acetylene esters to form a wide array of bicyclic amino acid derivatives, thus enabling the simultaneous functionalization of two vicinal C(sp3)?H bonds.