Synthesis, Table of Contents PAPER© Georg Thieme Verlag Stuttgart ˙ New YorkHydrophosphonylation of Benzoylhydrazones Using Iodine as a Catalyst: A Facile Synthesis of α-(N′-Acylhydrazino)-Substituted Phosphonates [¹] Biswanath Das*, Jayprakash Narayan Kumar, Avula Satya Kumar, Boddu Shashi KanthOrganic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, IndiaFax: +91(40)27193198; e-Mail: biswanathdas@yahoo.com; Recommend Article Abstract Buy Article All articles of this category Abstract A simple and efficient method for the synthesis of α-(N′-acylhydrazino)-substituted phosphonates has been developed using the hydrophosphonylation of benzoylhydrazones with triethyl phosphite in the presence of iodine as a catalyst at room temperature. The products are formed in excellent yields (89-95%) within two to three hours. Key words hydrophosphonylation - benzoylhydrazones - triethyl phosphite - α-(N′-acylhydrazino)-substituted phosphonates - iodine Full Text References References<A NAME="RZ11610SS-1">1</A> Part 205 in the series ‘Studies on Novel Synthetic Methodologies’. <A NAME="RZ11610SS-2">2</A> Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activities Kukhar VP. Hudson HR. John Wiley & Sons; New York: 2000. <A NAME="RZ11610SS-3A">3a</A> Augustyns K, Joossens J, van der Veken P, Lambeir A.-MVR, Scharpe S, and Haemers A. inventors; WO 2007045496. <A NAME="RZ11610SS-3B">3b</A> Alonso E. Alonso E. Solis A. del Pozo C. Synlett 2000, 698 <A NAME="RZ11610SS-3C">3c</A> Meyer JH. Barlett PA. J. Am. Chem. Soc. 1998, 120: 4600 <A NAME="RZ11610SS-4A">4a</A> Allen MC. Fuhrer W. Tuck B. Wade R. Wood JM. J. Med. Chem. 1989, 32: 1652 <A NAME="RZ11610SS-4B">4b</A> Bartlett PA. Hanson JE. Giannousis PG. J. Org. Chem. 1990, 55: 6268 <A NAME="RZ11610SS-4C">4c</A> Kafarski P. Lejezak B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63: 193 <A NAME="RZ11610SS-5A">5a</A> Atherton FR. Hasall CH. Lambert RW. J. Med. Chem. 1986, 29: 29 <A NAME="RZ11610SS-5B">5b</A> Bonarska D. Kleszczynska H. Sarapak J. Cell Mol. Biol. Lett. 2002, 7: 929 <A NAME="RZ11610SS-5C">5c</A> Smith WW. Bartlett PA. J. Am. Chem. Soc. 1998, 120: 4622 <A NAME="RZ11610SS-5D">5d</A> Emsley J. Hall D. The Chemistry of Phosphorus Harper Row; London: 1976. p.494 <A NAME="RZ11610SS-6A">6a</A> Changtao Q. Taishing H. J. Org. Chem. 1998, 63: 4125 <A NAME="RZ11610SS-6B">6b</A> Ranu B. Hjra A. Jana H. Org. Lett. 1999, 1: 1141 <A NAME="RZ11610SS-6C">6c</A> Manabe K. Kobayashi S. Chem. Commun. 2000, 669 <A NAME="RZ11610SS-6D">6d</A> Yadav JS. Reddy BVS. Sreedhar P. Green Chem. 2002, 4: 436 <A NAME="RZ11610SS-6E">6e</A> Saidi MR. Azizi N. Synlett 2002, 1347 <A NAME="RZ11610SS-6F">6f</A> Joly GD. Jacobsen EN. J. Am. Chem. Soc. 2004, 126: 4102 <A NAME="RZ11610SS-6G">6g</A> Pawar VD. Bettigeri S. Weng S.-S. Kao J.-Q. Chen C.-T. J. Am. Chem. Soc. 2006, 128: 6308 <A NAME="RZ11610SS-6H">6h</A> Saito B. Egami H. Katsuki T. J. Am. Chem. Soc. 2007, 129: 1978 <A NAME="RZ11610SS-6I">6i</A> Bhagat S. Chakraborthi AK. J. Org. Chem. 2007, 72: 1263 <A NAME="RZ11610SS-6J">6j</A> Merino P. Marques-Lopez E. Herrera RP. Adv. Synth. Catal. 2008, 350: 1195 <A NAME="RZ11610SS-7A">7a</A> Inokawa S. Nakatsukasa Y. Horisaki M. Yamashita M. Yoshida H. Ogata T. Synthesis 1977, 179 <A NAME="RZ11610SS-7B">7b</A> Yamashita M. Takeuchi J. Nakatani K. Oshikawa T. Bull. Chem. Soc. Jpn. 1985, 58: 377 <A NAME="RZ11610SS-7C">7c</A> Yamamoto H. Hanaya T. Kawamoto H. Inokawa S. Chem. Lett. 1989, 121 <A NAME="RZ11610SS-8A">8a</A> Heydari A. Javidan A. Schaffie M. Tetrahedron Lett. 2001, 42: 8071 <A NAME="RZ11610SS-8B">8b</A> Heydari A. Mehrdad M. Schaffie M. Abdolrezaie MS. Hajinassirei R. Chem. Lett. 2002, 1146 <A NAME="RZ11610SS-8C">8c</A> Heydari A. Arafi A. Catal. Commun. 2007, 8: 1023 <A NAME="RZ11610SS-9">9</A> Sugiura M. Kobayashi S. Angew. Chem. Int. Ed. 2005, 44: 5176 <A NAME="RZ11610SS-10">10</A> Rabasso N. Fadel A. Synthesis 2008, 2353 <A NAME="RZ11610SS-11">11</A> Herrera RP. Roca-Lopez D. Navarro-Moros G. Eur. J. Org. Chem. 2010, 1450 <A NAME="RZ11610SS-12A">12a</A> Das B. Damodar K. Bhunia N. Kanth BS. Tetrahedron Lett. 2009, 50: 2072 <A NAME="RZ11610SS-12B">12b</A> Das B. Damodar K. Bhunia N. J. Org. Chem. 2009, 74: 5607 <A NAME="RZ11610SS-12C">12c</A> Das B. Balasubramanyam P. Veeranjaneyulu B. Reddy CR. J. Org. Chem. 2009, 74: 9505 <A NAME="RZ11610SS-12D">12d</A> Das B. Satyalakshmi G. Suneel K. Tetrahedron Lett. 2009, 50: 2770