Heteroatom Chemistry Volume 22, Number 5, 2011 Synthesis of New Phosphonato Esters by Reaction between Triphenyl or Trialkyl Phosphite and Acetylenic Diesters in the Presence of NH-Containing Compounds Ghasem Marandi, 1 Malek Taher Maghsoodlou, 1 Nourallah Hazeri, 1 Reza Heydari, 1 Sayyed Mostafa Habibi-Khorassani, 1 Niloufar Akbarzadeh Torbati, 1 Seyed Sajad Sajadikhah, 1 Danial Saravani, 1 Mansoureh Rakhshanipour, 1 Samira Gholamipour, 1 Faramarz Rostami-Charati, 2 Brian W. Skelton, 3 Mohamed Makha, 3 Zeynab Zare, 1 and Mojtaba Lashkari 1 1 Department of Chemistry, The University of Sistan & Baluchestan, P. O. Box: 98135-674, Zahedan, Iran 2 Department of Chemistry, Faculty of Science, Gonbad Kavous University, P.O. Box 163, Gonbad, Iran 3 Chemistry, School of Biomedical, Biomolecular and Chemical Sciences, M313, University of Western Australia, Perth, WA 6009, Australia Received 18 November 2010; revised 19 February 2011 ABSTRACT: The reaction between triphenyl or trialkyl phosphite and acetylenic esters in the pres- ence of some heterocyclic or aromatic NH com- pounds such as thiazolidine-2,4-dione, 2-methyl in- dole, 5-bromoisatine, 3-nitroacetanilide, saccharin, 5,5-dimethylhydantoin, 2-nitroaniline, 4-nitroaniline, benzophenon hydrazine, and anthranilic acid led to the formation of phosphonato esters in high yield. C  2011 Wiley Periodicals, Inc. Heteroatom Chem 22:630– 639, 2011; View this article online at wileyonlineli- brary.com. DOI 10.1002/hc.20725 Correspondence to: M. T. Maghsoodlou; e-mail: mt maghsoodlou@yahoo.com. Contract grant sponsor: Research Council of the University of Sistan & Baluchestan. c  2011 Wiley Periodicals, Inc. INTRODUCTION Heterocyclic systems with oxygen, nitrogen, sulfur, and other heteroatoms in five- and six-membered rings, and also phosphorus compounds, are of in- terest due to their pharmaceutical and biological activities such as anti-inflammatory, cardiotonic, inotropic, antihypertensive, antimicrobial, and an- tibacterial properties [1–15]. Numerous studies have been previously reported using the reaction be- tween trivalent phosphorus nucleophiles and defi- cient carbonyl compounds, in the presence of a pro- ton source, such as CH, NH, OH, or SH compounds [16–30]. Continuing a series of investigations made on the development of organophosphorus heterocyclic compound synthesis [22–30], we now describe a one- pot synthesis of heterocyclic and aromatic phos- phonato ester derivatives 4a–f, 5a–g, and 7, using 630