Issue 21, 2010
From the journal:

Organic & Biomolecular Chemistry

Diastereoselective syntheses of 3-aryl-5-(arylalkyl)-6-methyl-1-(1-phenylethyl)thioxotetrahydropyrimidin-4(1H)-ones: A stereochemical perspective from endo and exocyclic chiral centres†

Varun Kumar,a   Pallepogu Raghavaiah,b   Shaikh M. Mobinc  and  Vipin A. Nair*a  

* Corresponding authors

a Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Sector 67, Mohali, Punjab 160 062, India
E-mail: vn74nr@yahoo.com
Tel: +91-172-2292045

b National Single Crystal X-ray Diffractometer Facility, School of Chemistry, University of Hyderabad, Hyderabad 500 046, India

c National Single Crystal X-ray Diffraction Facility, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India

Abstract

Diastereoselective syntheses of 3-aryl-(S/R)-6-methyl-1-[(S/R)-1-phenylethyl)]-2-thioxotetrahydro pyrimidin-4(1H)-ones were achieved in good yields by the condensation of aryl isothiocyanates with ethyl 3-(1-phenylethylamino)butanoate in a one-pot reaction. Benzylation of these substrates illustrated that the orientations of the exocylic and endocylic groups determine the stereochemical outcome of the product formed.

Graphical abstract: Diastereoselective syntheses of 3-aryl-5-(arylalkyl)-6-methyl-1-(1-phenylethyl)thioxotetrahydropyrimidin-4(1H)-ones: A stereochemical perspective from endo and exocyclic chiral centres

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Article information

DOI
https://doi.org/10.1039/C0OB00230E
Article type
Paper
Submitted
08 Jun 2010
Accepted
04 Aug 2010
First published
02 Sep 2010

Org. Biomol. Chem., 2010,8, 4960-4970

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Diastereoselective syntheses of 3-aryl-5-(arylalkyl)-6-methyl-1-(1-phenylethyl)thioxotetrahydropyrimidin-4(1H)-ones: A stereochemical perspective from endo and exocyclic chiral centres

V. Kumar, P. Raghavaiah, S. M. Mobin and V. A. Nair, Org. Biomol. Chem., 2010, 8, 4960 DOI: 10.1039/C0OB00230E

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