Affiliation:
1. Department of Chemistry, Bharath Institute of Higher Education and Research, Selaiyur, Chennai, Tamil Nadu, India
Abstract
<p>A new class of chiral pyrrolidinone was synthesized from (5S)-5-[(trityloxy)methyl] pyrrolidin-2-one (6) (Schemes 1 and 2). The synthetic design followed led to the insertion of various substituents at 1 and 5 of the pyrrolidinone moiety. Some of them possess two or three stereo centers, here configuration was retained under the mild condition. The new compounds also carry an imidazole moiety, which, along with the 2-pyrrolidinone template, may prove pivotal to several biological processes. The chiral pyrrolidinone (R) ring is incorporatedin various compounds with biological and pharmaceutical activities [1]. some of them are well known medicines, e.g., doxapram for patients with respiratory failure,piracetam for patients with Alzheimer’s seizures, and senile dementia, concussion and other neurological problems [2,3]. The properties and applications of pyroglutamic acid as a versatile building block in asymmetric synthesis has extensively been reviewed in the literature[4,5]. Some of them exhibited anti-inflammatory and antihypertensive activity [6,7]</p>
Reference10 articles.
1. F. Felluga, V. Gombac, G. Pitacco, E. Valentin, E. Zangrando, S. Morganti, E. Rizzato, D. Spinelli, G. Petrillo, Tetrahedron 2006, 62, 8787 – 8791.
2. Singh, P.; Dimitriou, V.; Malajan, R.P.; Crossley, A.W. Double-blind comparison between doxapram and pethidine in the treatment of postanaesthetic shivering. Br. J. Anaesth. 1993, 71, 685–688.
3. Winbal, B. Piracetam: A review of pharmacological properties and clinical uses. CNS Drug Rev. 2005, 11, 169–182
4. Panday, S.K.; Prasad, J.; Dikshit, K.D. Pyroglutamic acid: A unique chiral synthon. Tetrahedron: Asymmetry 2009, 20, 1581–1632.
5. Coppola, G.M.; Schuster, H.F. Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids; John Wiley: New York, NY, USA, 1987