A Novel Route to 1,2,3-Thiadiazole, 1,3,4-Thiadiazine, and 1,2,5-Triazepine Derivatives

Barbara Zaleska; Bartosz Trzewik; Jacek Grochowski; Paweł Serda

doi:10.1055/s-2003-42414

PAPER

A Novel Route to 1,2,3-Thiadiazole, 1,3,4-Thiadiazine, and 1,2,5-Triazepine Derivatives

Barbara Zaleska*^a, Bartosz Trzewik^a, Jacek Grochowski^b, Paweł Serda^b
^a Department of Organic Chemistry, Jagiellonian University, ul. Romana Ingardena 3, 30-060 Kraków, Poland
Fax: 48(12)6340515; e-Mail: zaleska@chemia.uj.edu.pl;
^b Regional Laboratory of Physicochemical Analyses and Structural Research, ul. Romana Ingardena 3, 30-060 Kraków, Poland

Abstract

Alle Artikel dieser Rubrik

Abstract

New convenient methods for the synthesis of 1,2,3-thiadiazole, 1,3,4-thiadiazine, and 1,2,5-triazepine derivatives are reported. In the heterocyclization process, the reactivity of 1-thia-4-aza-1,3-butadiene system of syn-2-phenylhydrazono-3-oxothiobutanoic acid anilides was exploited.

Key words

ring closure - heterocycles - cyclizations - thiadiazole - thiadiazine - triazepine

Volltext

Referenzen

References

<A NAME="RZ09703SS-1A">1a</A> Cyra ski MK. Krygowski TM. Katritzky AR. von Schleyer P. J. Org. Chem. 2002, 67: 1333

<A NAME="RZ09703SS-1B">1b</A> Glossman-Mitnik D. THEOCHEM 2001, 549: 285

<A NAME="RZ09703SS-2A">2a</A> Shafiee A. Jalilian AR. Rezaei M. J. Heterocycl. Chem. 2000, 37: 1325

<A NAME="RZ09703SS-2B">2b</A> Naidu AV. Dave MA. Asian. J. Chem. 2000, 687

<A NAME="RZ09703SS-3A">3a</A> Abramov MA. Dehaen W. D’hooge B. Petrov ML. Smeet S. Toppet S. Voets M. Tetrahedron 2000, 56: 3933

<A NAME="RZ09703SS-3B">3b</A> Hameurlaine A. Abramov MA. Dehaen W. Tetrahedron Lett. 2002, 43: 1015

<A NAME="RZ09703SS-4">4</A> Zhang Z, Yan J, Leung D, Wang S, Costello PC, and Sanghera J. inventors; US 6420400. ; Chem. Abstr. 2002, 137, 93758p

<A NAME="RZ09703SS-5">5</A> Schwarz M, Page P, Pomel V, Quattropani A, and Thomas RJ. inventors; PCT Int. Appl. WO 02102799. ; Chem. Abstr. 2003, 138, 55968v

<A NAME="RZ09703SS-6A">6a</A> Shin KJ. Koo KD. Yoo KH. Kang YK. Park WS. Kim DJ. Bioorg. Med. Chem. Lett. 2001, 11: 2397

<A NAME="RZ09703SS-6B">6b</A> Yamamoto H. Terasawa T. Nakamura A. Kawabata K. Takasugi H. Tanaka H. Matsumoto S. Matsumoto Y. Tawara S. Bioorg. Med. Chem. 2001, 9: 465

<A NAME="RZ09703SS-7A">7a</A> Fujii K, Hatano K, and Yoshida J. inventors; Jpn. Kokai Tokkyo Koho JP 2001 335570. ; Chem. Abstr. 2002, 136, 20074g

<A NAME="RZ09703SS-7B">7b</A> Lindell S, Dickhaut J, Jakobi H, Tiebes J, Jans D, Thoenessen M.-T, and Waibel JM. inventors; Eur. Pat. Appl. EP 1236727. ; Chem. Abstr. 2002, 137, 201314b

<A NAME="RZ09703SS-7C">7c</A> Uchikurohashi T, Tashima T, Yamamoto Y, Otsuka T, Yamaguchi R, and Imano T. inventors; Jpn. Kokai Tokkyo Koho JP 2002 114612. ; Chem. Abstr. 2002, 136, 305521n

<A NAME="RZ09703SS-8A">8a</A> Shibamoto S. J. Chem. Soc., Perkin Trans. 1 1992, 3233

<A NAME="RZ09703SS-8B">8b</A> Bianchi M. Butti A. Rossi S. Tetrahedron 1974, 30: 2765

<A NAME="RZ09703SS-9">9</A> Zaleska B. Bazanek T. Socha R. Karelus M. Grochowski J. Serda P. J. Org. Chem. 2002, 67: 4526

<A NAME="RZ09703SS-10">10</A> Zaleska B. Socha R. Monatsh. Chem. 2000, 131: 1151

<A NAME="RZ09703SS-11">11</A> Zaleska B. Socha R. Ciechanowicz-Rutkowska M. Pilati T. Monatsh. Chem. 2000, 131: 1158

<A NAME="RZ09703SS-12">12</A> Zaleska B. Socha R. Grochowski J. Serda P. Szneler E. J. Org. Chem. 2003, 68: 2334

<A NAME="RZ09703SS-13">13</A> Zaleska B. Cie¿ D. Haas A. Synth. Commun. 1996, 26: 4165

Compound 2a crystallizes in the monoclinic system. See experimental for details of X-ray structure determination. The structural data have been deposited at the Cambridge Crystallographic Data Centre under the reference number CCDC 209483.