Simple and efficient one-pot synthesis of 2-substituted benzoxazole and benzothiazole

Synthetic Communications

Volumn 40, Issue 2, 2010, Pages 206-212

  Patil, Sachin S ^a   Bobade, Vivek D ^a  

^a Department of Chemistry   (India)

Author keywords

2 Aminophenol; 2 aminothiophenol; Benzoxazole; Diethyl bromo phoshonate; Tert butyl hypochlorite

Indexed keywords

2 AMINOPHENOL; 2 AMINOTHIOPHENOL; ALDEHYDE; BENZOTHIAZOLE; BENZOXAZOLE DERIVATIVE; DIETHYLBROMOPHOSPHONATE; OXIDIZING AGENT; REAGENT; TERT BUTYLHYPOCHLORITE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ONE POT SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 73949091992     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902906602     Document Type: Article

References (25)

1. (a) Deluca, M. R.; Kerwin, S. M. Total synthesis of UK-1. Tetrahedron Lett. 1997, 38, 199-202;
2. (b) Temiz, O.; Oren, I.; Sener, E.; Yalcin, I.; Ucartark, N. Synthesis and microbiological activity of some novel 5-or 6-methyl-2-(2, 4-disubstituted phenyl)benzoxazole derivatives. Farmaco 1998, 53, 337-341;
3. (c) Sato, S.; Kajiiura, T.; Noguchi, M.; Takehana, K.; Kobayash, T.; Tsujii, T. AJI9561, a new cyctotoxic benzoxazole derivatives produced by Streptomyces sp. J. Antibiot. 2001, 54, 102-104.
4. (a) Katsura, Y.; Nishino, S.; Inoue, Y.; Tomol, M.; Takasugi, H. Studies on antiulcer drug: Synthesis and antiulcer activity of imidazo [1,2a] pyridinyl-2-allyl amino benzoxa-zole and 5,6,7,8 tetrahydroimidazo [1,2a] pyridyl derivatives. Chem. Pharm. Bull. 1992, 40, 371-380;
5. 2-receptor antagonist. Chem. Pharm. Bull. 1992, 40, 1424-1438.
6. Haugwitz, R. D.; Angel, R. G.; Jacobs, G. A.; Maurev, B. V.; Narayanan, V. L.; Cruthers, L. R.; Szanto, J. Synthesis and anthelmintic activity of novel 2-heteroaromatic-substituted isothiocyanato benzoxazole and benzothiazole. J. Med. Chem. 1982, 25, 969-974.
7. Ueki, M.; Ueno, K.; Miyadoh, S.; Abe, K.; Shibata, K.; Taniguchi, M.; Oi, S. UK-1, a novel cyctotoxic metabolites from Streptomyces sp. 517-02. J. Antibiot. 1993, 46, 1089-1094.
8. Edward, P. D.; Zottola, M. A.; Davis, M.; Williams, J.; Tuthill, P. A. Peptidyl a-ketohe-terocyclic inhibitors of human neutrophil elastase 3. In vitro and in vivo potency of a series of peptidyl a-ketobenzoxazole. J. Med. Chem. 1995, 38, 3972-3982.
9. Kashiyama, E.; Huchinson, I.; Chau, M. S.; Stinson, S. F.; Phillips, L. R.; Kaur, G.; Sausville, E. A.; Bradshaw, T. D.; Westwell, A. D.; Stevens, M. F. G. Antitumor benzothiazole-synthesis, metabolic formation, and biological properties of the C-and N-oxidation product of antitumor 2-(4-aminophenyl) benzothiazoles. J. Med. Chem. 1999, 42, 4172-4184.
10. Bradshaw, T. D.; Stevens, M. F. G.; Westwell, A. D. The discovery of the potent and selective antitumor agent 2-(4-amino-3-methyl phenyl) benzothiazole (DF 203) and related compounds. Curr. Med. Chem. 2001, 8, 203-210.
11. Terashima, M.; Ishii, M. Facile synthesis of 2-substituted benzoxazole. Synthesis 1982, 1484-1485.
12. Ben-Alloum, A.; Bakkas, S.; Soufiaoui, M. Nouvelle voie de Synthèsedes: 2-Arylben-̀ zothiazoles Transfertd Electrons Activèe par Micro-ondes. Tetrahedron Lett. 1997, 38, 6395-6396.
13. Srivastava, R. G.; Venkatramani, P. S. Barium manganate oxidation in organic synthesis. Synth. Comm. 1998, 18, 1537-1544.
14. Stephens, F. F.; Bower, J. D. The preparation of benzimidazole and benzoxazole from Schiff's base. J. Chem. Soc. 1949, 2971-2972.
15. Nakagawa, K.; Onoue, H.; Sugita, J. Oxidation with nickel peroxide, IV: The preparation of benzoxazoles from Schiff's bases. Chem. Pharm. Bull. 1964, 12, 1135-1138.
16. Park, K. H.; Jun, K.; Shin, S. R.; Oh, S. W. 2-Aryl benzoxazole from phenolic Schiff's bases by thianthrene cation radical. Tetrahedron Lett. 1996, 37, 8869-8870.
17. Varma, R. S.; Saini, R. K.; Prakash, O. Hypervalent iodine oxidation of phenolic Schiff's bases: Synthesis of 2-arylbenzoxazoles. Tetrahedron Lett. 1997, 38, 2621-2622. (Pubitemid 27154349)
18. Varma, R. S.; Kumar, D. J. Manganese triacetate oxidation of phenolic Schiff's bases: Synthesis of 2-aryl benzoxazole. Heterocycle. Chem. 1998, 35, 1539-1540.
19. Bougrin, K.; Loupy, A.; Souflaouj, M. Trios Nouvelles Voles de Synthese des derive 1, 3 azoliques Sous micro-ondes. Tetrahedron 1998, 54, 8055-8064.
20. Praveen, C.; Hemanth Kumar, K.; Murlidharan, D.; Perumal, P. T. Oxidative cyclization of thiophenolic and phenolic Schiff's bases promoted by PCC: A new oxidant for 2-substituted benzothiazoles and benzoxazoles. Tetrahedron 2008, 64, 2369-2374.
21. (a) Viirre, R.; Evinder, G.; Batey, R. A. Copper catalysed domino annulation approach to the synthesis of benzoxazole under microwave accelerated and conventional thermal condition. J. Org. Chem. 2008, 73, 3452-3459;
22. (b) Benedi, C.; Bravo, F.; Uriz, P.; Fernandez, E.; Claver, C.; Castillon, S. Synthesis of 2-substituted-benzothiazoles by palladium-catalyzed intramolecular cyclization of o-bromophenylthioureas and o- bromophenylthioamides. Tetrahedron Lett. 2003, 44, 6073-6077;
23. (c) Joyce, L. L.; Evinder, G.; Batey, R. A. Copper and palladium catalysed intramolecular C-S bond formation: A convient synthesis of 2-amino benzothiazole. Chem. Commun. 2004, 446-447.
24. Garst, M. E.; Sachs, G. Prodrugs of proton pump inhibitors. US Patent 6559167, 2003.
25. Arote, N. D.; Akamanchi, K. G. Direct conversion of aldehydes to acyl azides using tert-butyl hypochlorite. Tetrahedron Lett. 2007, 48, 5661-5664.