Simple and Efficient One-Pot Synthesis of 2-Substituted Benzoxazole and Benzothiazole

REFERENCES

• (a) Deluca , M. R. ; Kerwin , S. M. Total synthesis of UK-1 . Tetrahedron Lett. 1997 , 38 , 199 – 202 ; (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 ; (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 .
   Web of Science ®Google Scholar
• (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 benzoxazole and 5,6,7,8 tetrahydroimidazo [1,2a] pyridyl derivatives. Chem. Pharm. Bull. 1992, 40, 371–380; (b) Katsura , Y. ; Nishino , S. ; Inoue , Y. ; Tomol , M. ; Takasugi , H. Studies on antiulcer drug III: Synthesis and antiulcer activity of imidazo [1,2a] pyridinyl ethyl benzoxazole and related compound: A novel class of histamin H2-receptor antagonist. Chem. Pharm. Bull. 1992, 40, 1424–1438.
   PubMed Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• Edward , P. D. ; Zottola , M. A. ; Davis , M. ; Williams , J. ; Tuthill , P. A. Peptidyl α-ketoheterocyclic inhibitors of human neutrophil elastase 3. In vitro and in vivo potency of a series of peptidyl α-ketobenzoxazole . J. Med. Chem. 1995 , 38 , 3972 – 3982 .
   PubMed Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• Terashima , M. ; Ishii , M. Facile synthesis of 2-substituted benzoxazole . Synthesis 1982 , 1484 – 1485 .
   Google Scholar
• Ben-Alloum , A. ; Bakkas , S. ; Soufiaoui , M. Nouvelle voie de Synthèsedes: 2-Arylbenzothiazoles Transfert[ddot] Electrons Activèe par Micro-ondes . Tetrahedron Lett. 1997 , 38 , 6395 – 6396 .
   Web of Science ®Google Scholar
• Srivastava , R. G. ; Venkatramani , P. S. Barium manganate oxidation in organic synthesis . Synth. Comm. 1998 , 18 , 1537 – 1544 .
   Web of Science ®Google Scholar
• Stephens , F. F. ; Bower , J. D. The preparation of benzimidazole and benzoxazole from Schiff's base . J. Chem. Soc. 1949 , 2971 – 2972 .
   Web of Science ®Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Bougrin , K. ; Loupy , A. ; Souflaouj , M. Trios Nouvelles Voles de Synthese des derive 1, 3 azoliques Sous micro-ondes . Tetrahedron 1998 , 54 , 8055 – 8064 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• (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 ; (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 ; (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 .
   PubMed Web of Science ®Google Scholar
• Garst , M. E. ; Sachs , G. Prodrugs of proton pump inhibitors. US Patent 6559167, 2003 .
   Google Scholar
• Arote , N. D. ; Akamanchi , K. G. Direct conversion of aldehydes to acyl azides using tert-butyl hypochlorite . Tetrahedron Lett. 2007 , 48 , 5661 – 5664 .
   Web of Science ®Google Scholar