ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Regioselective N-alkylation of (2-chloroquinolin-3-yl) methanol with N-heterocyclic compounds using the Mitsunobu reagent

Selvaraj Mohana Roopan, Fazlur-Rahman Nawaz Khan, and Jong Sung Jin

Organic & Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore, Tamil Nadu, 632 014 India

E-mail: nawaz_f@yahoo.co.in

Abstract: The Mitsunobu reaction is a well-established fundamental reaction and has been widely applied in organic synthesis. In this paper, under Mitsunobu conditions dehydration proceeds between (2-chloroquinolin-3-yl)methanol and nitrogen heterocyclic compounds such as quinazolinone, pyrimidone, 2-oxoquinoline in dry THF in the presence of triethylamine, triphenylphosphane and diethyl azodicarboxylate to give the corresponding products. As part of our recent research, we attempted to couple two N-heterocyclic compounds under Mitsunobu reaction conditions to provide efficient building blocks for natural product synthesis.

Keywords: Mitsunobu reaction – N-heterocyclic compounds – (2-chloroquinolin-3-yl)methanol – DEAD – P(Ph)3 – THF

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-011-0018-1

Chemical Papers 65 (3) 345–351 (2011)