Simple, Convenient and Heterogeneous Method for Conversion of Urazoles to Triazolinediones Using N,N,N′,N′-Tetrabromobenzene-1,3-disulfonylamide or Trichloromelamine under Mild and Heterogeneous Conditions

Mohammad Ali Zolfigol; Ramin Ghorbani-Vaghei; Shadpour Mallakpour; Gholamabbas Chehardoli; Arash Ghorbani Choghamarani; Amaneh Hosain Yazdi

doi:10.1055/s-2006-926446

PAPER

Simple, Convenient and Heterogeneous Method for Conversion of Urazoles to Triazolinediones Using N,N,N′,N′-Tetrabromobenzene-1,3-disulfonylamide or Trichloromelamine under Mild and Heterogeneous Conditions

Mohammad Ali Zolfigol*^a, Ramin Ghorbani-Vaghei^a, Shadpour Mallakpour^b, Gholamabbas Chehardoli^a, Arash Ghorbani Choghamarani^a, Amaneh Hosain Yazdi^a
^a Department of Chemistry, College of Science, Bu-Ali Sina University, P. O. Box 4135, Hamadan 65174, Iran
e-Mail: Zolfi@basu.ac.ir;
^b Organic Polymer Chemistry Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran

Abstract

All articles of this category

Abstract

N,N,N′,N′-Tetrabromobenzene-1,3-disulfonylamide (TBBDA) or trichloromelamine (TCM) were used as effective oxidizing agents for the oxidation of urazoles and bisurazoles to their corresponding triazolinediones under mild and heterogeneous conditions at room temperature with excellent yields.

Key words

N,N,N′,N′-tetrabromobenzene-1,3-disulfonylamide - trichloromelamine - urazoles - bisurazoles - triazolinediones

Full Text

References

<A NAME="RZ24105SS-1A">1a</A> Mallakpour SE. Zolfigol MA. Indian J. Chem., Sect B: Org. Chem. Incl. Med. Chem. 1995, 34: 183

<A NAME="RZ24105SS-1B">1b</A> Mallakpour SE. Zolfigol MA. Indian J. Chem., Sect B: Org. Chem. Incl. Med. Chem. 1995, 34: 302

<A NAME="RZ24105SS-1C">1c</A> Mallakpour SE. Zolfigol MA. Indian J. Chem., Sect B: Org. Chem. Incl. Med. Chem. 1998, 37: 1001

<A NAME="RZ24105SS-1D">1d</A> Mallakpour SE. Zolfigol MA. Indian J. Chem., Sect B: Org. Chem. Incl. Med. Chem. 1999, 38: 777

<A NAME="RZ24105SS-2">2</A> Desimoni G. Faita G. Righetti PP. Sulcini A. Tsyganov D. Tetrahedron 1994, 50: 1821

<A NAME="RZ24105SS-3A">3a</A> Hall JH. Krishnan G. J. Org. Chem. 1984, 49: 2498

<A NAME="RZ24105SS-3B">3b</A> Hall JH. Jones ML. J. Org. Chem. 1983, 48: 822

<A NAME="RZ24105SS-3C">3c</A> Seymour GA. Green FD. J. Am. Chem. Soc. 1980, 102: 6384

<A NAME="RZ24105SS-4A">4a</A> Mallakpour SE. Butler GB. Aghabozorg H. Palenik GJ. Macromol. 1985, 18: 342

<A NAME="RZ24105SS-4B">4b</A> Lai YC. Mallakpour SE. Butler GB. Palanik G. J. Org. Chem. 1985, 50: 4378

<A NAME="RZ24105SS-4C">4c</A> Vougioukalakis GC. Orfanopoulos M. Synlett 2005, 713

<A NAME="RZ24105SS-5A">5a</A> Mallakpour SE. Butler GB. J. Polym. Sci., Part A: Polym. Chem. Ed. 1989, 27: 217

<A NAME="RZ24105SS-5B">5b</A> Mallakpour SE. Butler GB. J. Polym. Sci., Part A: Polym. Chem. Ed. 1989, 27: 125

<A NAME="RZ24105SS-5C">5c</A> Mallakpour SE. Butler GB. J. Polym. Sci., Part A: Polym. Chem. Ed. 1987, 25: 2781

<A NAME="RZ24105SS-6">6</A> Wilson RM. Hengge AC. Ataei A. Ho DM. J. Am. Chem. Soc. 1991, 113: 1240

<A NAME="RZ24105SS-7">7</A> Wilson RM. Chantarasiri N. J. Am. Chem. Soc. 1991, 113: 2301

<A NAME="RZ24105SS-8">8</A> Klindert T. Seitz G. Synth. Commun. 1996, 26: 2587

<A NAME="RZ24105SS-9A">9a</A> Cookson RC. Stevens IDR. Watts CT. J. Chem. Soc., Chem. Commun. 1966, 744

<A NAME="RZ24105SS-9B">9b</A> Borhani DW. Green FD. J. Org. Chem. 1986, 51: 1563

<A NAME="RZ24105SS-9C">9c</A> Akasaka T. Sonobe H. Sato R. Ando W. Tetrahedron Lett. 1984, 25: 4757

<A NAME="RZ24105SS-10A">10a</A> Zolfigol MA. Choghamarani AG. Shahamirian M. Safaiee M. Mohammadpoor-Baltork I. Mallakpour SE. Abdollahi-Alibeik M. Tetrahedron Lett. 2005, 46: 5581

<A NAME="RZ24105SS-10B">10b</A> Zolfigol MA. Azarifar D. Mallakpour SE. Mohammadpoor-Baltork I. Forghaniha A. Maleki B. Abdollahi-Alibeik M. Tetrahedron Lett. 2006, 47: 833

<A NAME="RZ24105SS-11">11</A> Stickler JC. Pirkle WH. J. Org. Chem. 1966, 31: 3444

<A NAME="RZ24105SS-12">12</A> Read G. Rechardson NR. J. Chem. Soc., Perkin Trans. 1 1996, 167

<A NAME="RZ24105SS-13">13</A> Arya VP. Shenoy S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1976, 14: 883

<A NAME="RZ24105SS-14">14</A> Warnho H. Wald K. Org. Prep. Proced. Int. 1975, 7: 251

<A NAME="RZ24105SS-15">15</A> Mallakpour SE. J. Chem. Educ. 1992, 69: 238

<A NAME="RZ24105SS-16">16</A> Mallakpour SE. Zolfigol MA. J. Sci., Islamic Repub. Iran 1993, 4: 199

<A NAME="RZ24105SS-17A">17a</A> Zolfigol MA. Mallakpour SE. Madrakian E. Ghaemi E. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2000, 39: 308

<A NAME="RZ24105SS-17B">17b</A> Zolfigol MA. Zebarjadian MH. Chehardoli G. Mallakpour SE. Shamsipur M. Tetrahedron 2001, 57: 1627

<A NAME="RZ24105SS-17C">17c</A> Zolfigol MA. Chehardoli G. Mallakpour SE. Nasr-Isfahani H. Synth. Commun. 2001, 31: 1965

<A NAME="RZ24105SS-17D">17d</A> Zolfigol MA. Torabi M. Mallakpour SE. Tetrahedron 2001, 57: 8381

<A NAME="RZ24105SS-17E">17e</A> Hajipour AR. Mallakpour SE. Zolfigol MA. Adibi H. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2002, 41: 2425

<A NAME="RZ24105SS-17F">17f</A> Zolfigol MA. Chehardoli G. Mallakpour SE. Synth. Commun. 2003, 33: 833

<A NAME="RZ24105SS-18A">18a</A> Zolfigol MA. Bagherzadeh M. Chehardoli G. Mallakpour SE. Mamaghani M. J. Chem. Res., Synop 2001, 390

<A NAME="RZ24105SS-18B">18b</A> Zolfigol MA. Mallakpour SE. Madrakian E. Ghaemi E. Synlett 2002, 1633

<A NAME="RZ24105SS-18C">18c</A> Zolfigol MA. Salehi P. Mallakpour SE. Torabi M. Bull. Chem. Soc. Jpn. 2003, 76: 1673

<A NAME="RZ24105SS-19A">19a</A> Zolfigol MA. Nassr-Isfahani H. Mallakpour SE. Safaiee M. Synlett 2005, 761

<A NAME="RZ24105SS-19B">19b</A> Ghorbani-Vaghei R. Khazaei A. Tetrahedron Lett. 2003, 44: 7525

<A NAME="RZ24105SS-19C">19c</A> Ghorbani-Vaghei R. Azarifar D. Maleki B. Bull. Korean Chem. Soc. 2004, 25: 953

<A NAME="RZ24105SS-19D">19d</A> Zolfigol MA. Mallakpour S. Khazaei A. Ghorbani-Vaghei R. Torabi M. Bull. Korean Chem. Soc. 2004, 25: 1251

<A NAME="RZ24105SS-20">20</A> Ghorbani-Vaghei R. Jalili H. Synthesis 2005, 1099

These compounds are sensitive to light, heat, alcohols, ethers, transition metals, and any nucleophiles. Also, they are very volatile - if the temperature rises over 50 °C in the course of removing of CH₂Cl₂, some TADs are removed with the solvent simultaneously. Therefore, the temperature must be controlled and CH₂Cl₂ is the best solvent for this purpose.

<A NAME="RZ24105SS-22A">22a</A> Zolfigol MA. Tetrahedron 2001, 57: 9509 ; see Scheme 5

<A NAME="RZ24105SS-22B">22b</A> Zolfigol MA. Mohammadpoor-Baltork I. Mirjalili BF. Bamoniri A. Synlett 2003, 1877

<A NAME="RZ24105SS-22C">22c</A> Zolfigol MA. Shirini F. Choghamarani AG. Mohammadpoor-Baltork I. Green Chem. 2002, 4: 562

<A NAME="RZ24105SS-22D">22d</A> Chen W.-Y. Lu J. Synlett 2005, 2293

<A NAME="RZ24105SS-22E">22e</A> Salehi P. Dabiri M. Zolfigol MA. Baghbanzadeh M. Synlett 2005, 1155

<A NAME="RZ24105SS-22F">22f</A> Salehi P. Dabiri M. Zolfigol MA. Baghbanzadeh M. Tetrahedron Lett. 2005, 46: 7051

<A NAME="RZ24105SS-22G">22g</A> Zolfigol MA. Bamoniri A. Synlett 2002, 1621

<A NAME="RZ24105SS-22H">22h</A> Salehi P. Dabiri M. Zolfigol MA. Bodaghifard MA. Tetrahedron Lett. 2003, 44: 2889

<A NAME="RZ24105SS-22I">22i</A> Azizian J. Karimi AR. Kazemizadeh Z. Mohammadi AA. Mohammadizadeh MR. Synthesis 2005, 1095

<A NAME="RZ24105SS-22J">22j</A> Khodaei MM. Khosropour AR. Fattahpour P. Tetrahedron Lett. 2005, 46: 2105

<A NAME="RZ24105SS-22K">22k</A> Yakaiah T. Reddy GV. Lingaiah BPV. Narsaiah B. Shanthan Rao P. Synth. Commun. 2005, 35: 1307

<A NAME="RZ24105SS-22L">22l</A> Hajipour AR. Mirjalili BF. Zarei A. Khazdooz L. Ruoho AE. Tetrahedron Lett. 2004, 45: 6607

<A NAME="RZ24105SS-22M">22m</A> Shaabani A. Soleimani K. Bazgir A. Synth. Commun. 2004, 34: 3315