Solvent-free synthesis of 2-aryl and 2-alkylbenzothiazoles on silica gel under microwave irradiation

Synthetic Communications

Volumn 34, Issue 16, 2004, Pages 3029-3036

  Kodomari, Mitsuo ^a   Tamaru, Yoshimi ^a   Aoyama, Tadashi ^b  

^a SHIBAURA INSTITUTE OF TECHNOLOGY   (Japan)

^b NIHON UNIVERSITY   (Japan)

Author keywords

2 Alkylbenzothiazole; 2 Arylbenzothiazole; Microwave irradiation; Silica gel

Indexed keywords

2 AMINOTHIOPHENOL; ALDEHYDE; BENZOTHIAZOLE DERIVATIVE; SILICA GEL; SOLVENT; THIOPHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MICROWAVE IRRADIATION; POLYMERIZATION;

EID: 4544382219     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200026663     Document Type: Article

References (18)

1. Bradshaw, T.D.; Wrigley, S.; Shi, D.-F.; Schultz, R.J.; Paull, K.D.; Stevens, M.F.G. 2-(4-Aminophenyl)benzothiazoles on growth of human oxarion carcinoma cells in vitro and in vivo. Br. J. Cancer 1998, 77, 745.
2. (a) Cassidy, P.E. In Thermally Stable Polymer; Marcel Dekker: New York, 1980;
3. (b) Wang, S.; Bao, G.; Lu, Z.; Wu, P.; Han, Z. Effect of heat treatment on the structure and properties of poly(2,6-benzothiazole)(ABPBT) and poly(2,5-benzoxazole)(ABPBO). J. Mater. Sci. 2000, 35, 5873.
4. Deligeorgiev, T.G. An improved method for the preparation of 2-aryl-, 2-hetaryl- and 2-styrylbenzothiazoles. Dyes and Pigments 1990, 12, 243.
5. Hein, D.W.; Alheim, R.J.; Leavitt, J.J. The use of polyphosphoric acid in the synthesis of 2-aryl- and 2-alkyl-substituted benzoimidazoles, benzoxazoles, and benzothiazoles. J. Am. Chem. Soc. 1957, 79, 427.
6. Kanaoka, Y.; Hamada, T.; Yonemitsu, O. Polyphosphate ester as a synthetic agent. XIII. Synthesis of 2-substituted benzoxazoles with PPE. Chem. Pharm. Bull. 1970, 18, 587.
7. Boger, D.L. A convenient preparation of 2-substituted benzothiazoles. J. Org. Chem. 1978, 43, 2296.
8. Hutchinson, I.; Stevens, M.G.F.; Westwell, A.D. The regiospecific synthesis of 5- and 7-monosubstituted and 5,6-disubstituted 2- arylbenzothiozoles. Tetrahedron Lett. 2000, 41, 425.
9. So, Y.-H.; DeCaire, R. 2-Arylbenzothiazoles and 2-arylbenzoxazoles from α,α,α,-trihalomethyl aromatic compounds. Synth. Commun. 1998, 28, 4123.
10. Perry, R.J.; Wilson, B.D. Palladium-catalyzed synthesis of 2-arylbenzothiazoles. Organometallics 1994, 13, 3346.
11. Zhong, W.; Chen, X.; Zhang, Y. Low-valent titanium induced simultaneous reduction of nitro group and S-S bond in nitrodisulfides: A novel method for the synthesis of benzothiazoline, benzothiazoles and 2,3-dihydro-1,5- benzothiazepines. Synth. Commun. 2000, 30, 4451.
12. Tale, R.H. Novel synthesis of 2-arylbenzothiazoles mediated by ceric ammonium nitrate (CAN). Org. Lett. 2002, 4, 1641.
13. Loupy, A., Ed. Microwaves in Organic Synthesis; Wiley-VCH: Weinheim, 2002.
14. Varma, R.S. Solvent-free organic synthesis using supported reagents and microwave irradiation. Green Chem. 1999, 43.
15. Villemin, D.; Hammadi, M.; Martin, B. Clay catlysis: Condensation of orthoesters with o-substituted aminoaromatics into heterocycles. Synth. Commun. 1996, 26, 2895.
16. Bougrin, K.; Loupy, A.; Soufiaoui, M. Trois nouvelles voise de synthese des derives 1,3-azoliques sous micro-ondes. Tetrahedron 1998, 54, 8055.
17. Poul, S.; Gupta, M.; Gupta, R. Microwave-induced solvent-free synthesis of 2-arylbenzothiazoles using p-TsOH. Synth. Commun. 2002, 32, 3541.
18. Rann, B.C.; Jana, R.; Dey, S.S. An efficient and green synthesis of 2-arylbenzothiazoles in an ionic liquid, [pmIb]Br under microwave irradiation. Chem. Lett. 2004, 33, 274.