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An Efficient One‐Pot Synthesis of Chiral N‐Protected 3‐Substituted (Diketo)piperazines via Ugi‐4CR/De‐Boc/Cyclization Process
Author(s) -
Jida Mouhamad,
Ballet Steven
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702943
Subject(s) - diketopiperazines , combinatorial chemistry , acetic acid , chemistry , filtration (mathematics) , one pot synthesis , organic chemistry , catalysis , mathematics , statistics
A convenient and high yielding method to prepare a vast array of enantiomerically pure 3‐substituted diketopiperazines (3‐DKPs), bearing a benzyl protecting group on nitrogen 1 is reported. The methodology describes a simple one‐pot procedure, starting from readily available N‐protected L‐ or D‐amino acids employing the Ugi‐4CR in pure water, followed by a one‐step Boc‐deprotection and final lactamisation in acetic acid. All disubstituted DKPs were obtained in short times and isolated in excellent yields (84‐94%) by simple precipitation in water and subsequent filtration. The practical utility of this procedure proved efficient for the synthesis of cialis (Tadalafil) analogues.