Trichloroisocyanuric Acid/NaNO2 as a Novel Heterogeneous System for the N-Nitrosation of N,N-Dialkylamines Under Mild Conditions

Mohammad Ali Zolfigol; Arash Ghorbani Choghamarani; Hassan Hazarkhani

doi:10.1055/s-2002-31897

LETTER

Trichloroisocyanuric Acid/NaNO₂ as a Novel Heterogeneous System for the N-Nitrosation of N,N-Dialkylamines Under Mild Conditions

Mohammad Ali Zolfigol*^a, Arash Ghorbani Choghamarani^a, Hassan Hazarkhani^b
^a Chemistry Department, College of Science, Bu-Ali Sina University, Hamadan, Zip Code 65174, Iran
^b Chemistry Department, Institute for Advanced Studies in Basic Sciences (IASBS), P. O. Box 45195-159, Gava Zang, Zanjan, Iran
e-Mail: Zolfi@basu.ac.ir;

Abstract

All articles of this category

Abstract

A combination of trichloroisocyanuric acid and sodium nitrite in the presence of wet SiO₂ was used as an effective nitrosating agent for the nitrosation of N,N-dialkyl amines to their corresponding nitroso derivatives under mild and heterogeneous conditions in moderate to excellent yields.

Key words

trichloroisocyanuric acid - nitrosation - secondary amines - N-nitroso amines

Full Text

References

<A NAME="RD06202ST-1A">1a</A> Williams DLH. Nitrosation Cambridge University Press; Cambridge: 1988. p.77

<A NAME="RD06202ST-1B">1b</A> Williams DLH. Supplement F2, In The Chemistry of Amino, Nitroso, Nitro and Related Groups John Wiley and Sons Ltd; New York: 1996. p.665

<A NAME="RD06202ST-1C">1c</A> Keefer LK. Williams DLH. Methods in Nitric Oxide Reseach John Wiley and Sons Ltd; New York: 1996. p.509 ; and references cited therein

<A NAME="RD06202ST-2">2</A> Garcia-Rio L. Leis JR. Moreira JA. Norberto F. J. Org. Chem. 2001, 66: 381

<A NAME="RD06202ST-3">3</A> Garcia-Rio L. Leis JR. Iglesias E. J. Org. Chem. 1997, 62: 4712

<A NAME="RD06202ST-4">4</A> Nudelman NS. Bonatti AE. Synlett 2000, 1825 ; and references cited therein

<A NAME="RD06202ST-5">5</A> Olszewska T. Milewska MJ. Gdaniec M. Matuszynska H. Potonski T. J. Org. Chem. 2001, 66: 501

<A NAME="RD06202ST-6">6</A> Zolfigol MA. Shirini F. Ghorbani Choghamarani A. Taqian-nasab A. Keypour H. Salehzadeh S. J. Chem. Res., Synop. 2000, 420

<A NAME="RD06202ST-7">7</A> Rivera A. Gallo GI. Joseph-Nathan P. Synth. Commun. 1997, 27: 163

<A NAME="RD06202ST-8A">8a</A> Furniss B. S., Hannaford A. J., Smith P. W. G., Tatchell A. R.; Vogels Text Book of Practical Organic Chemistry; Longman: London and New York, 1989; 5th ed.:

<A NAME="RD06202ST-8B">8b</A> Sheriner RL. Reynold TL. Fuson C. Curtin DY. Morrill TC. The Systematic Identification of Organic Compounds 6th ed.: John Wiley and Sons; New York: 1980. p.220

<A NAME="RD06202ST-9">9</A> Castedo L. Riguera R. Vezquez MP. J. Chem. Soc., Chem. Commun. 1983, 301

<A NAME="RD06202ST-10">10</A> Fanning JC. Keefer LK. Larry K. J. Chem. Soc., Chem. Commun. 1987, 955

<A NAME="RD06202ST-11">11</A> Nakajima M. Warner JC. Anselme JP. Tetrahedron Lett. 1984, 25: 2619

<A NAME="RD06202ST-12">12</A> Chang SK. Hrrington GW. Rothstein M. Shergalis WA. Swern D. Vohra SK. Cancer Res. 1979, 39: 3871

<A NAME="RD06202ST-13">13</A> Makhova NN. Karpov GA. Mikhailyuk AN. Bova AE. KhmelŽnitskii LI. Novikov SS. Izv. Akad. Nauk SSSR, Ser. Khim. 1978, 1: 226

<A NAME="RD06202ST-14">14</A> Zolfigol MA. Synth. Commun. 1999, 29: 905 ; and references cited therein

<A NAME="RD06202ST-15A">15a</A> Zolfigol MA. Ghorbani Choghamarani A. Shirini F. Keypour H. Salehzadeh S. Synth. Commun. 2001, 31: 359

<A NAME="RD06202ST-15B">15b</A> Zolfigol MA. Shirini F. Ghorbani Choghamarani A. Shiri A. Keypour H. Salehzadeh S. Asian J. Chem. 2001, 13: 849

<A NAME="RD06202ST-16">16</A> Zolfigol MA. Tetrahedron 2001, 57: 9509 ; and our references cited therein

<A NAME="RD06202ST-17A">17a</A> Firouzabadi H. Iranpoor N. Hazarkhani H. Synlett 2001, 1641 ; and references cited therein

<A NAME="RD06202ST-17B">17b</A> Xiog Z. Xuang NP. Zhong P. Synth. Commun. 2001, 31: 245

<A NAME="RD06202ST-18">18</A> Singer SS. Lijinsky W. Singer GM. Tetrahedron Lett. 1977, 19: 1613

<A NAME="RD06202ST-19">19</A> Singer SS. J. Org. Chem. 1978, 43: 4612

<A NAME="RD06202ST-20">20</A> Turnbull K. J. Heterocycl. Chem. 1985, 22: 965

<A NAME="RD06202ST-21">21</A> Richter-Addo GB. Acc. Chem. Res. 1999, 32: 529

<A NAME="RD06202ST-22">22</A> Zolfigol MA. Zebarjadian MH. Chehardoli GA. Keypour H. Salehzadeh S. Shamsipur M. J. Org. Chem. 2001, 66: 3619

<A NAME="RD06202ST-23">23</A> Zolfigol MA. Zebarjadian MH. Sadeghi MM. Memarian HR. Mohammadpoor-Baltork I. Shamsipur M. Synth. Commun. 2001, 30: 929

<A NAME="RD06202ST-24">24</A> Zolfigol MA. Zebarjadian MH. Chehardoli G. Mallakpour SE. Shamsipur M. Tetrahedron 2001, 57: 1627