A new synthesis of 4H-1,4-benzothiazine derivatives based on ring closure of EWG-stabilized (2-isocyanophenylthio)methyl anions

Synthesis

Volumn , Issue 7, 2006, Pages 1077-1082

  Kobayashi, Kazuhiro ^a   Hayashi, Kazutaka ^a   Iitsuka, Daisuke ^a   Morikawa, Osamu ^a   Konishi, Hisatoshi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

Benzothiazine; Carbanion; Heterocycle; Isocyanide; Ring closure

Indexed keywords

CYANIDES; HYDROGEN; METHANOL; NEGATIVE IONS; POTASSIUM COMPOUNDS; SODIUM COMPOUNDS; SULFUR;

BENZOTHIAZINE; CARBANIONS; HETEROCYCLES; ISOCYANIDES; RING CLOSURE;

ORGANIC POLYMERS;

2 CYANO (2 NITROPHENYL)METHYLTHIOPHENYL ISOCYANIDE; 2 CYANO (4 NITROPHENYL)METHYLTHIOPHENYL ISOCYANIDE; 2 CYANO (PHENYLSULFINYL)METHYLTHIOPHENYL ISOCYANIDE; 2 NITROPHENOL; 4 NITROPHENOL; ANION; BENZONITRILE; BENZOTHIAZINE DERIVATIVE; BUTANE; CYANIDE; HYDROGEN; METHYL GROUP; POTASSIUM DERIVATIVE; POTASSIUM TERT BUTOXIDE; PROTON; SODIUM; SULFUR; THIOL GROUP; UNCLASSIFIED DRUG;

ARTICLE; DEHYDROGENATION; DEPROTONATION; PROTON TRANSPORT; RING CLOSING METATHESIS; SYNTHESIS;

EID: 33645996416     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926385     Document Type: Article

References (10)

1. For biological activities of 4H-1,4-benzothiazine derivatives, see: (a) Armenise, D.; Trapani, G.; Arrivo, V.; Laraspata, E.; Morlacchi, F. J. Heterocycl. Chem. 2000, 37, 1611.
2. (b) Cecchetti, V.; Calderone, V.; Tabarrini, O.; Sabatini, S.; Filipponi, E.; Testai, L.; Spogli, R.; Martinotti, E.; Fravolini, A. J. Med. Chem. 2003, 46, 3670.
3. For previous reports on the synthesis and biological activity of 4H-1,4-benzothiazine-2-carbonitrile derivatives, see: (c) Kano, S.; Yuasa, Y.; Ono, T.; Shibuya, S. Heterocycles 1979, 12, 681.
4. (d) Liso, G.; Trapani, G.; Berardi, V.; Latrofa, A.; Marchini, P. J. Heterocycl. Chem. 1980, 17, 793.
5. (e) Schou, S. C.; Hànsen, H. C.; Tagmose, T. M.; Boonen, H. C. M.; Worsaae, A.; Drabowski, M.; Wahl, P.; Arkhammar, P. O. G.; Bodvarsdottir, T.; Antonine, M.-H.; Lebrun, P.; Hansen, J. B. Bioorg. Med. Chem. 2005, 13, 141.
6. (a) Pippich, S.; Bartsch, H. Heterocycles 1996, 43, 1967.
7. (b) Gupta, R.; Verma, P. S.; Gupta, R. R. Heterocycl. Commun. 1998, 5, 479.
8. (c) Sharma, P. R.; Gupta, V.; Gautam, D. C.; Gupta, R. R. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 1483; and references cited therein.
9. Kay, D. P.; Kennewell, P. D.; Westwood, R. J. Chem. Soc., Perkin Trans. 1 1982, 1879.
10. Cadman, M. L. F.; Crombie, L.; Freeman, S.; Mistry, J. J. Chem. Soc., Perkin Trans. 1 1995, 1397.