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
References
1a Cyra MK.
Krygowski TM.
Katritzky AR.
von Schleyer P.
J. Org. Chem.
2002,
67:
1333
1b Glossman-Mitnik D.
THEOCHEM
2001,
549:
285
2a Shafiee A.
Jalilian AR.
Rezaei M.
J. Heterocycl. Chem.
2000,
37:
1325
2b Naidu AV.
Dave MA.
Asian. J. Chem.
2000,
687
3a Abramov MA.
Dehaen W.
D’hooge B.
Petrov ML.
Smeet S.
Toppet S.
Voets M.
Tetrahedron
2000,
56:
3933
3b Hameurlaine A.
Abramov MA.
Dehaen W.
Tetrahedron Lett.
2002,
43:
1015
4 Zhang Z, Yan J, Leung D, Wang S, Costello PC, and Sanghera J. inventors; US 6420400.
; Chem. Abstr. 2002 , 137 , 93758p
5 Schwarz M, Page P, Pomel V, Quattropani A, and Thomas RJ. inventors; PCT Int. Appl. WO 02102799.
; Chem. Abstr. 2003 , 138 , 55968v
6a Shin KJ.
Koo KD.
Yoo KH.
Kang YK.
Park WS.
Kim DJ.
Bioorg. Med. Chem. Lett.
2001,
11:
2397
6b Yamamoto H.
Terasawa T.
Nakamura A.
Kawabata K.
Takasugi H.
Tanaka H.
Matsumoto S.
Matsumoto Y.
Tawara S.
Bioorg. Med. Chem.
2001,
9:
465
7a Fujii K, Hatano K, and Yoshida J. inventors; Jpn. Kokai Tokkyo Koho JP 2001 335570.
; Chem. Abstr. 2002 , 136 , 20074g
7b 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
7c 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
8a Shibamoto S.
J. Chem. Soc., Perkin Trans. 1
1992,
3233
8b Bianchi M.
Butti A.
Rossi S.
Tetrahedron
1974,
30:
2765
9 Zaleska B.
Bazanek T.
Socha R.
Karelus M.
Grochowski J.
Serda P.
J. Org. Chem.
2002,
67:
4526
10 Zaleska B.
Socha R.
Monatsh. Chem.
2000,
131:
1151
11 Zaleska B.
Socha R.
Ciechanowicz-Rutkowska M.
Pilati T.
Monatsh. Chem.
2000,
131:
1158
12 Zaleska B.
Socha R.
Grochowski J.
Serda P.
Szneler E.
J. Org. Chem.
2003,
68:
2334
13 Zaleska B.
Cie¿ D.
Haas A.
Synth. Commun.
1996,
26:
4165
14 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.
