Tin(IV) Chloride-Sodium Nitrite as a New Nitrosating Agent for N-Nitrosa­tion of Amines, Amides and Ureas under Mild and Heterogeneous Conditions

Benoît Célariès; Cyril Párkányi

doi:10.1055/s-2006-942397

PAPER

Tin(IV) Chloride-Sodium Nitrite as a New Nitrosating Agent for N-Nitrosation of Amines, Amides and Ureas under Mild and Heterogeneous Conditions

Benoît Célariès, Cyril Párkányi*
Department of Chemistry and Biochemistry, Florida Atlantic University, 777 Glades Road, P. O. Box 3091, Boca Raton, FL 33431-0991, USA
Fax: +1(561)2972759; e-Mail: parkanyi@fau.edu;

Abstract

All articles of this category

Abstract

We have developed a new method of N-nitrosation of various secondary and tertiary amines, amides and ureas using a mixture of tin(IV) chloride and sodium nitrate. This method leads to a selective, high-yielding and mild heterogeneous N-nitrosation by in situ generation of nitrosyl chloride (NOCl). The reaction can be carried out in several different solvents such as chloroform, dichloromethane, ethers, ethyl acetate and alcohols, at room temperature.

Key words

tin(IV) chloride - N-nitrosation - nitrosamines - nitrosoureas - nitrosamides

Full Text

References

<A NAME="RM00606SS-1A">1a</A> Nathan C. Shiloh MU. Proc. Nat. Acad. Sci. USA 2000, 97: 8841

<A NAME="RM00606SS-1B">1b</A> Poole RK. Hughes MN. Mol. Microbiol. 2000, 36: 775

<A NAME="RM00606SS-1C">1c</A> Woodmansee AN. Imlay JA. Mol. Microbiol. 2003, 49: 11

<A NAME="RM00606SS-1D">1d</A> Bruckdorfer R. Mol. Aspects Med. 2005, 26: 3

<A NAME="RM00606SS-2A">2a</A> Moncada S. Palmer RM. Higgs EA. Pharmacol. Rev. 1991, 43: 109

<A NAME="RM00606SS-2B">2b</A> Bartsch H. Montesano R. Carcinogenesis 1984, 5: 1381

<A NAME="RM00606SS-3A">3a</A> Wang PG. Xian M. Tang X. Wu X. Wen Z. Cai T. Janczuk AJ. Chem. Rev. 2002, 102: 1091

<A NAME="RM00606SS-3B">3b</A> Nitric Oxide Donors for Pharmaceutical and Biological Applications Wang PG. Cai TB. Taniguchi N. Wiley-VCH Verlag GmbH & Co. KGaA; Weinheim: 2005.

<A NAME="RM00606SS-4A">4a</A> Schabel FM. Johnston TP. McCaleb GS. Montgomery JA. Laster WR. Skipper HE. Cancer (Philadelphia) 1963, 23: 725

<A NAME="RM00606SS-4B">4b</A> Unger C. Eibl H. Von Heyden HW. Krisch B. Nagel GA. Klin. Wochenschr. 1985, 63: 565

<A NAME="RM00606SS-5A">5a</A> Oh SMNYF. Williams DLH. J. Chem. Soc., Perkin Trans. 2 1989, 755

<A NAME="RM00606SS-5B">5b</A> Castro A. Leis JR. Pena ME. J. Chem. Soc., Perkin Trans. 2 1989, 1861

<A NAME="RM00606SS-5C">5c</A> Galtress CL. Morrow PR. Nag S. Smalley TL. Tschantz MF. Vaughn JS. Wichems DN. Ziglar SK. Fishbein JC. J. Am. Chem. Soc. 1992, 114: 1406

<A NAME="RM00606SS-5D">5d</A> Santala T. Fishbein JC. J. Am. Chem. Soc. 1992, 114: 8852

<A NAME="RM00606SS-6A">6a</A> Berger MR. Schmähl D. Zerban H. Carcinogenesis 1987, 8: 1635

<A NAME="RM00606SS-6B">6b</A> Bartsch H. Montesano R. Carcinogenesis 1984, 5: 1381

<A NAME="RM00606SS-7">7</A> Lijinsky W. Chemistry and Biology of N-Nitroso Compounds Cambridge University Press; Cambridge, England: 1992.

<A NAME="RM00606SS-8A">8a</A> Seebach D. Enders D. Angew. Chem., Int. Ed. Engl. 1975, 14: 15

<A NAME="RM00606SS-8B">8b</A> Seebach D. Enders D. Angew. Chem., Int. Ed. Engl. 1972, 11: 1101

<A NAME="RM00606SS-8C">8c</A> Seebach D. Enders D. Angew. Chem., Int. Ed. Engl. 1972, 11: 1102

<A NAME="RM00606SS-8D">8d</A> Challis BC. Challis JA. In The Chemistry of Amino, Nitroso, and Nitro Compounds and Their Derivatives Suppl. F., Part 2: Patai S. Wiley; New York: 1982. Chap. 26.

<A NAME="RM00606SS-8E">8e</A> Fraser RR. Passannanti S. Synthesis 1976, 540

<A NAME="RM00606SS-8F">8f</A> Enders D. Hassel T. Pieterr R. Renger B. Seebach D. Synthesis 1976, 548

<A NAME="RM00606SS-8G">8g</A> Seebach D. Wykypiel W. Synthesis 1979, 423

<A NAME="RM00606SS-9">9</A> Kostyukovskii YL. Melamed DB. Russ. Chem. Rev. 1988, 57: 350

<A NAME="RM00606SS-10A">10a</A> Williams DLH. Nitrosation Reactions and the Chemistry of Nitric Oxide 1st ed.: Elsevier Science Pub Co; Amsterdam, Oxford: 2004.

<A NAME="RM00606SS-10B">10b</A> Turney TA. Wright GA. Chem. Rev. 1959, 59: 497

<A NAME="RM00606SS-11A">11a</A> Ridd JH. Adv. Phys. Org. Chem. 1978, 16: 1

<A NAME="RM00606SS-11B">11b</A> Castro A. Leis JR. Peña ME. J. Chem. Res., Synop. 1986, 216

<A NAME="RM00606SS-11C">11c</A> Casado J. Castro A. Leis JR. Lopez-Quintela MA. Mosquera M. Monatsh. Chem. 1983, 114: 639

<A NAME="RM00606SS-12">12</A> Garcia Rio L. Leis JR. Iglesias E. J. Org. Chem. 1997, 62: 4701

<A NAME="RM00606SS-13A">13a</A> Leis JR. Peña ME. Rios A. J. Chem. Soc., Perkin Trans. 2. 1993, 1233

<A NAME="RM00606SS-13B">13b</A> Leis JR. Peña ME. Rios A. J. Chem. Soc., Perkin Trans. 2 1995, 587

<A NAME="RM00606SS-14">14</A> Uppu RM. Squadrito GL. Bolzan RM. Pryor WA. J. Am. Chem. Soc. 2000, 122: 6911

<A NAME="RM00606SS-15">15</A> Castedo L. Riguera R. Vazquez MP. J. Chem. Soc., Chem. Commun. 1983, 301

<A NAME="RM00606SS-16">16</A> Chang SK. Harrington GW. Rothstein M. Shergalis WA. Swern D. Vohra SK. Cancer Res. 1979, 39: 3871

<A NAME="RM00606SS-17">17</A> Cova D. Nebuloni C. Arnoldi A. Bassoli A. Trevisan M. Del Re AAM. J. Agric. Food. Chem. 1996, 44: 2852

<A NAME="RM00606SS-18A">18a</A> Zolfigol MA. Choghamarani AG. Hazarkhani H. Synlett 2002, 1002

<A NAME="RM00606SS-18B">18b</A> Zolfigol MA. Synth. Commun. 1999, 29: 905

<A NAME="RM00606SS-18C">18c</A> Zolfigol MA. Nematollahi D. Mallakpour SE. Synth. Commun. 1999, 29: 2277

<A NAME="RM00606SS-18D">18d</A> Zolfigol MA. Shirini F. Choghamarani AG. Synth. Commun. 2002, 32: 1809

<A NAME="RM00606SS-18E">18e</A> Zolfigol MA. Bamoniri A. Synlett 2002, 1621

<A NAME="RM00606SS-18F">18f</A> Zolfigol MA. Habibi D. Mirjalili BF. Bamoniri A. Tetrahedron Lett. 2003, 44: 3345

<A NAME="RM00606SS-18G">18g</A> Zolfigol MA. Shirini F. Choghamarani AG. Taqian-Nasab A. Keypour H. Salezadeh S. J. Chem. Res., Synop. 2000, 9: 420

<A NAME="RM00606SS-18H">18h</A> Zolfigol MA. Choghamarani AG. Shirini F. Keypour H. Salehzadeh S. Synth. Commun. 2001, 31: 359

<A NAME="RM00606SS-18I">18i</A> Zolfigol MA. Shirini F. Choghamarani AG. Shiri A. Keypour H. Salehzadeh S. Asian J. Chem. 2001, 13: 849

<A NAME="RM00606SS-19A">19a</A> Iranpoor N. Firouzabadi H. Heydari R. J. Chem. Res., Synop. 1999, 668

<A NAME="RM00606SS-19B">19b</A> Zolfigol MA. Zabarjadian MH. Chehardoli G. Keypour H. Salehzadeh S. Shamsipur M. J. Org. Chem. 2001, 66: 3619

<A NAME="RM00606SS-20">20</A> Iranpoor N. Firouzabadi H. Pourali A.-R. Synthesis 2003, 1591

<A NAME="RM00606SS-21">21</A> Iranpoor N. Firouzabadi H. Pourali A.-R. Synth. Commun. 2005, 35: 1517

<A NAME="RM00606SS-22">22</A> Fanning JC. Keefer LK. Larry K. J. Chem. Soc., Chem. Commun. 1987, 955

<A NAME="RM00606SS-23">23</A> Demir AS. Mahasneh AS. Aksoy H. Gercek Z. Synth. Commun. 1992, 22: 2607

<A NAME="RM00606SS-24">24</A> Kang Y. Zyryanov GV. Rudkevich DM. Chem. Eur. J. 2005, 11: 1924

<A NAME="RM00606SS-25A">25a</A> Williams DLH. Nitrosation Cambridge University Press; Cambridge: 1988.

<A NAME="RM00606SS-25B">25b</A> Casado J. Lorenzo FM. Mosquera M. Prieto MFR. Can. J. Chem. 1984, 62: 136

<A NAME="RM00606SS-26">26</A> Guo Z. McGill A. Yu L. Ramirez J. Wang PG. Bioorg. Med. Chem. Lett. 1996, 6: 573

<A NAME="RM00606SS-27">27</A> Ranganathan D. Bamezai S. Saini S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1991, 30: 169

<A NAME="RM00606SS-28">28</A> Gowenlock BG. Hutchinson RJ. Little J. Pfab J. J. Chem. Soc., Perkin Trans. 2 1979, 1110

<A NAME="RM00606SS-29A">29a</A> Zaidi SSH. Khan MA. Yousufzai AHK. Pak. J. Sci. Ind. Res. 1972, 15: 13

<A NAME="RM00606SS-29B">29b</A> Olah GA. Donovan DJ. J. Org. Chem. 1978, 43: 1743

<A NAME="RM00606SS-30">30</A> CRC Handbook of Chemistry and Physics 80th ed.: Lide DR. CRC Press; Boca Raton: 1999.

<A NAME="RM00606SS-31">31</A> Torra N. Urpi F. Vilarrasa J. Tetrahedron 1989, 45: 863

<A NAME="RM00606SS-32">32</A> Weinkam RJ. Lin H.-S. J. Med. Chem. 1979, 22: 1193

<A NAME="RM00606SS-33">33</A> Lown JW. Chauhan SMS. J. Org. Chem. 1981, 46: 5309

<A NAME="RM00606SS-34A">34a</A> Lown JW. Chauhan SMS. J. Org. Chem. 1983, 48: 513

<A NAME="RM00606SS-34B">34b</A> Yamamoto M. Yamada T. Tanimura A. Chem. Pharm. Bull. 1983, 31: 3678

<A NAME="RM00606SS-35A">35a</A> Madelmont JC. Moreau MF. Godeneche D. Labarre P. Veyre A. J. Labelled Compd. Radiopharm. 1988, 25: 1135

<A NAME="RM00606SS-35B">35b</A> Gaudreault RC. Lacroix J. Page M. Joly LP. J. Pharm. Sci. 1988, 77: 185

<A NAME="RM00606SS-36">36</A> Martinez J. Oiry J. Imbach JL. Winternitz F. J. Med. Chem. 1982, 25: 178

<A NAME="RM00606SS-37">37</A> Sosnovsky G. Baysal M. Erciyas E. J. Pharm. Sci. 1994, 83: 999

<A NAME="RM00606SS-38A">38a</A> Iranpoor N. Firouzabadi H. Heydari R. Phosphorus, Sulfur Silicon 2003, 178: 1027

<A NAME="RM00606SS-38B">38b</A> Oae S. Kim YH. Fukushima D. Shinhama K. J. Chem. Soc., Perkin Trans. 1 1978, 913

<A NAME="RM00606SS-39A">39a</A> Oae S. Fukushima D. Kim YH. J. Chem. Soc., Chem. Commun. 1977, 407

<A NAME="RM00606SS-39B">39b</A> Kim YH. Shinhama K. Fukushima D. Oae S. Tetrahedron Lett. 1978, 14: 1211

Tin(IV) Chloride-Sodium Nitrite as a New Nitrosating Agent for N-Nitrosa­tion of Amines, Amides and Ureas under Mild and Heterogeneous Conditions

Tin(IV) Chloride-Sodium Nitrite as a New Nitrosating Agent for N-Nitrosation of Amines, Amides and Ureas under Mild and Heterogeneous Conditions