How to cite this paper
Sedaghat, N., Naimi-Jamal, M & Mokhtari, J. (2014). Solvent- and catalyst-free synthesis of 2-aryl(heteroaryl)-substituted benzothiazoles.Current Chemistry Letters, 3(2), 57-62.
Refrences
1. Horton D.A., Bourne, G.T., Smythe, M.L. (2003) The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem. Rev., 103, 893-930.
2. Palmer P.J., Trigg R.B., Warrington J.V. (1971) Benzothiazolines as antituberculous agents. J. Med. Chem., 14, 248-251.
3. Benazzouz A., Boraud T., Dubédat P., Boireau A., Stutzmann J.M., Gross C. (1995) Riluzole prevents MPTP-induced parkinsonism in the rhesus monkey: a pilot study, Eur. J. Pharmacol., 284, 299-307.
4. Bénéteau V., Besson T., Guillard J., Léonce S., Pfeiffer B. (1999) Synthesis and in vitro antitumour evaluation of benzothiazole-2-carbonitrile derivatives. Eur. J. Med. Chem., 34, 1053-1060
5. Ivanov S.K., Yuritsyn V.S. (1971) Neftekhimiya, 11, 99-107.
6. Ben-Alloum A., Bakkas S., Soufiaoui M. (1997) Nouvelle voie de synthèse des 2-arylbenzothiazoles transfert d & apos; electrons activé par micro-ondes. Tetrahedron Lett. 38, 6395-6396
7. Roe A., Tuker W.P. (1965) The preparation of some fluorobenzothiazoles. J. Heterocycl. Chem., 2, 148-151.
8. Hutchinson I., Stevens M.F.G., Westwell A.D. (2000) The regiospecific synthesis of 5- and 7-monosubstituted and 5,6-disubstituted 2-arylbenzothiazoles, Tetrahedron Lett., 41, 425-428.
9. (a) Paul S., Gupta M., Gupta R. (2002) Microwave-induced solvent-free synthesis of 2-arylbenzothiazoles using p–TsOH. Synth. Commun., 32, 3541-3547. (b) Weekes A.A., Dix M.C., Bagley M.C., Westwell A.D. (2010) Rapid and convenient thermal or microwave-assisted synthesis of substituted 2-phenylbenzothiazoles. Synth. Commun., 40, 3027-3032. (c) Mitsuo K., Tamaru Y., Aoyama T. (2004) Solvent-free synthesis of 2-aryl and 2-alkylbenzothiazoles on silica gel under microwave irradiation, Synth. Commun., 34, 3029-3036.
10. Majo V.J., Prabhakaran J., Mann J.J., Kumar J.S.D. (2003) An efficient palladium catalyzed synthesis of 2-arylbenzothiazoles, Tetrahedron Lett., 44, 8535-8537.
11. Heo Y., Song Y.S., Kim B.T., Heo J.N. (2006) A highly regioselective synthesis of 2-aryl-6-chlorobenzothiazoles employing microwave-promoted Suzuki–Miyaura coupling reaction, Tetrahedron Lett., 47, 3091-3094.
12. Alagille D., Baldwin R.M., Tamagnan G.D. (2005) One-step synthesis of 2-arylbenzothiazole (‘BTA’) and -benzoxazole precursors for in vivo imaging of B-amyloid plaques. Tetrahedron Lett., 46, 1349-1351.
13. Tale R.H. (2002) Novel Synthesis of 2-Arylbenzothiazoles Mediated by Ceric Ammonium Nitrate (CAN). Org. Lett., 4, 1641-1642
14. (a) Mokhtari J., Naimi-Jamal M.R., Hamzeali H., Dekamin M.G., Kaupp G. (2009) Kneading ball-milling and stoichiometric melts for the quantitative derivatization of carbonyl compounds with gas-solid recovery. ChemSusChem, 2, 248-254. (b) Kaupp G., Naimi-Jamal M.R., Schmeyers J. (2003) Solvent-free Knoevenagel condensations and Michael additions in the solid state and in the melt with quantitative yield. Tetrahedron, 59, 3753-3760. (c) Kaupp G., Naimi-Jamal M.R., Stepanenko V. (2003) Waste-free and facile solid-state protection of diamines, anthranilic acid, diols, and polyols with phenylboronic acid. Chem. Eur. J., 9, 4156-4160. (d) Mashkouri S., Naimi-Jamal M.R. (2009) Mechanochemical solvent-free and catalyst-free one-pot synthesis of pyrano[2,3-d]pyrimidine-2,4(1H,3H)-diones with quantitative yields. Molecules, 14, 474-479. (e) Naimi-Jamal M.R., Mashkouri S., Sharifi A. (2010) An efficient, multicomponent approach for solvent-free synthesis of 2-amino-4H-chromene scaffold. Mol. Div., 14, 473-477.
15. (a) Kodomari M., Tamara Y., Aoyama T. (2004) Solvent?free synthesis of 2?aryl and 2?alkylbenzothiazoles on silica gel under microwave irradiation. Synth. Commun., 34, 3029, (b) Fawzia A.Q., Mekheimer R.A., Sadek K.U. (2008) Cerium (IV) ammonium nitrate (CAN) catalyzed one-pot synthesis of 2-arylbenzothiazoles, Molecules, 13, 2908-2914.
16. (a) Boger L.A (1977) Convenient preparation of 2-substituted benzothiazoles. J. Org. Chem., 43, 11. (b) Stanetty P., Krumpak B. (1996) Novel synthesis of benzothiazole derivatives via directed lithiation and aryne-mediated cyclization followed by quenching with electrophiles. J. Org. Chem., 61, 5130-5133. (c) Tale R.H. (2002) Novel synthesis of 2-arylbenzothiazoles mediated by ceric ammonium nitrate (CAN). Org. Lett., 4, 1641-1642. (d) Dileep Kumar J.S., Mann J. (2003) An efficient palladium catalyzed synthesis of 2-arylbenzothiazoles, Tetrahedron Lett., 44, 8535-8537. (e) Weekes A.A., Dix M.C., Bagley M.C., Westwell A.D. (2010) Rapid and convenient thermal or Microwave-assisted synthesis of Substituted 2-phenylbenzothiazoles, Synth. Commun., 40, 3027-3032. (f) Hayashi M., Kawashita Y.A (2006) Simple synthesis of 2-arylbenzothiazoles and its application to palladium-catalyzed Mizoroki–Heck reaction, Tetrahedron Lett., 47, 4231-4233. (g) Idrees M., Bose S.A. (2007) Convenient access to substituted benzothiazole scaffolds via intramolecular cyclization of thioformanilides, Tetrahedron Lett., 48, 669-672.
2. Palmer P.J., Trigg R.B., Warrington J.V. (1971) Benzothiazolines as antituberculous agents. J. Med. Chem., 14, 248-251.
3. Benazzouz A., Boraud T., Dubédat P., Boireau A., Stutzmann J.M., Gross C. (1995) Riluzole prevents MPTP-induced parkinsonism in the rhesus monkey: a pilot study, Eur. J. Pharmacol., 284, 299-307.
4. Bénéteau V., Besson T., Guillard J., Léonce S., Pfeiffer B. (1999) Synthesis and in vitro antitumour evaluation of benzothiazole-2-carbonitrile derivatives. Eur. J. Med. Chem., 34, 1053-1060
5. Ivanov S.K., Yuritsyn V.S. (1971) Neftekhimiya, 11, 99-107.
6. Ben-Alloum A., Bakkas S., Soufiaoui M. (1997) Nouvelle voie de synthèse des 2-arylbenzothiazoles transfert d & apos; electrons activé par micro-ondes. Tetrahedron Lett. 38, 6395-6396
7. Roe A., Tuker W.P. (1965) The preparation of some fluorobenzothiazoles. J. Heterocycl. Chem., 2, 148-151.
8. Hutchinson I., Stevens M.F.G., Westwell A.D. (2000) The regiospecific synthesis of 5- and 7-monosubstituted and 5,6-disubstituted 2-arylbenzothiazoles, Tetrahedron Lett., 41, 425-428.
9. (a) Paul S., Gupta M., Gupta R. (2002) Microwave-induced solvent-free synthesis of 2-arylbenzothiazoles using p–TsOH. Synth. Commun., 32, 3541-3547. (b) Weekes A.A., Dix M.C., Bagley M.C., Westwell A.D. (2010) Rapid and convenient thermal or microwave-assisted synthesis of substituted 2-phenylbenzothiazoles. Synth. Commun., 40, 3027-3032. (c) Mitsuo K., Tamaru Y., Aoyama T. (2004) Solvent-free synthesis of 2-aryl and 2-alkylbenzothiazoles on silica gel under microwave irradiation, Synth. Commun., 34, 3029-3036.
10. Majo V.J., Prabhakaran J., Mann J.J., Kumar J.S.D. (2003) An efficient palladium catalyzed synthesis of 2-arylbenzothiazoles, Tetrahedron Lett., 44, 8535-8537.
11. Heo Y., Song Y.S., Kim B.T., Heo J.N. (2006) A highly regioselective synthesis of 2-aryl-6-chlorobenzothiazoles employing microwave-promoted Suzuki–Miyaura coupling reaction, Tetrahedron Lett., 47, 3091-3094.
12. Alagille D., Baldwin R.M., Tamagnan G.D. (2005) One-step synthesis of 2-arylbenzothiazole (‘BTA’) and -benzoxazole precursors for in vivo imaging of B-amyloid plaques. Tetrahedron Lett., 46, 1349-1351.
13. Tale R.H. (2002) Novel Synthesis of 2-Arylbenzothiazoles Mediated by Ceric Ammonium Nitrate (CAN). Org. Lett., 4, 1641-1642
14. (a) Mokhtari J., Naimi-Jamal M.R., Hamzeali H., Dekamin M.G., Kaupp G. (2009) Kneading ball-milling and stoichiometric melts for the quantitative derivatization of carbonyl compounds with gas-solid recovery. ChemSusChem, 2, 248-254. (b) Kaupp G., Naimi-Jamal M.R., Schmeyers J. (2003) Solvent-free Knoevenagel condensations and Michael additions in the solid state and in the melt with quantitative yield. Tetrahedron, 59, 3753-3760. (c) Kaupp G., Naimi-Jamal M.R., Stepanenko V. (2003) Waste-free and facile solid-state protection of diamines, anthranilic acid, diols, and polyols with phenylboronic acid. Chem. Eur. J., 9, 4156-4160. (d) Mashkouri S., Naimi-Jamal M.R. (2009) Mechanochemical solvent-free and catalyst-free one-pot synthesis of pyrano[2,3-d]pyrimidine-2,4(1H,3H)-diones with quantitative yields. Molecules, 14, 474-479. (e) Naimi-Jamal M.R., Mashkouri S., Sharifi A. (2010) An efficient, multicomponent approach for solvent-free synthesis of 2-amino-4H-chromene scaffold. Mol. Div., 14, 473-477.
15. (a) Kodomari M., Tamara Y., Aoyama T. (2004) Solvent?free synthesis of 2?aryl and 2?alkylbenzothiazoles on silica gel under microwave irradiation. Synth. Commun., 34, 3029, (b) Fawzia A.Q., Mekheimer R.A., Sadek K.U. (2008) Cerium (IV) ammonium nitrate (CAN) catalyzed one-pot synthesis of 2-arylbenzothiazoles, Molecules, 13, 2908-2914.
16. (a) Boger L.A (1977) Convenient preparation of 2-substituted benzothiazoles. J. Org. Chem., 43, 11. (b) Stanetty P., Krumpak B. (1996) Novel synthesis of benzothiazole derivatives via directed lithiation and aryne-mediated cyclization followed by quenching with electrophiles. J. Org. Chem., 61, 5130-5133. (c) Tale R.H. (2002) Novel synthesis of 2-arylbenzothiazoles mediated by ceric ammonium nitrate (CAN). Org. Lett., 4, 1641-1642. (d) Dileep Kumar J.S., Mann J. (2003) An efficient palladium catalyzed synthesis of 2-arylbenzothiazoles, Tetrahedron Lett., 44, 8535-8537. (e) Weekes A.A., Dix M.C., Bagley M.C., Westwell A.D. (2010) Rapid and convenient thermal or Microwave-assisted synthesis of Substituted 2-phenylbenzothiazoles, Synth. Commun., 40, 3027-3032. (f) Hayashi M., Kawashita Y.A (2006) Simple synthesis of 2-arylbenzothiazoles and its application to palladium-catalyzed Mizoroki–Heck reaction, Tetrahedron Lett., 47, 4231-4233. (g) Idrees M., Bose S.A. (2007) Convenient access to substituted benzothiazole scaffolds via intramolecular cyclization of thioformanilides, Tetrahedron Lett., 48, 669-672.