A new piperazine: Spectroscopic and theoretical conformational studies

Author(s)

Bueno, Marco A. ^[1] ; Moura, Rebeca G. ^[2] ; Franco, Mauricio ^[2] ; Braga, Ataualpa A. C. ^[2] ; Di Vitta, Claudio ^[2] ; Marzorati, Liliana ^[2]

Affiliation

^[1] Univ Fed ABC, Ctr Ciencias Nat & Humanas, Ave Estados 5001, BR-09210580 Santo Andre, SP - Brazil

^[2] Univ Sao Paulo, Inst Quim, Ave Prof Lineu Prestes 748, BR-05508900 Sao Paulo, SP - Brazil

• Document type: Journal article
• Source: Journal of Molecular Structure; v. 1203, MAR 5 2020.
• Web of Science Citations: 0

Abstract

The reaction of benzylamine with the N-tosylaziridine prepared from (S)-serine and bearing an amide group at C2 afforded a single open chain compound, in contrast to the lack of regioselectivity for the ring opening of the analogous 2-carbalkoxy derivative. The (S)-amide substituted piperazine was prepared by N,N'-bisalkylation of the corresponding open chain compound. Theoretical calculations for the piperazine and NMR experiments indicated that for all three most stable conformations the amide group is axially positioned. (C) 2019 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 15/01491-3 - Theoretical study of cross-coupling reactions: homogeneous and heterogeneous catalysis
• Grantee: Ataualpa Albert Carmo Braga
• Support Opportunities: Regular Research Grants
• FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
• Grantee: Carlos Roque Duarte Correia
• Support Opportunities: Research Projects - Thematic Grants