Methanesulfonic Acid/SiO₂ as an Efficient Combination for the Synthesis of 2-Substituted Aromatic and Aliphatic Benzothiazoles from Carboxylic Acids

REFERENCES

• Koci , J. ; Klimesova , V. ; Waisser , K. ; Kaustova , J. ; Dahse , H.-M. ; Mollmann , U. Heterocyclic benzazole derivatives with antimycobacterial in vitro activity . Bioorg. Med. Chem. Lett. 2002 , 12 , 3275 – 3278 .
   PubMed Web of Science ®Google Scholar
• (a) Palmer , P. J. ; Trigg , R. B. ; Warrington , J. V. Benzothiazolines as antituberculous agents . J. Med. Chem. 1971 , 14 , 248 – 251 ; (b) Ali , A. ; Taylor , G. E. ; Graham , D. W. Gram-positive selective antimicrobial compounds compositions containing such compounds and methods of treatment. PCT Int. Appl. 2001 , WO 2001028561 .
   PubMed Web of Science ®Google Scholar
• (a) Bradshaw , T. D. ; Wrigley , S. ; Shi , D. F. ; Schulz , R. J. ; Paull , K. D. ; Stevens , M. F. G. 2-(4-Aminophenyl)benzoxazoles on growth of humane orexin carcinoma cells in vivo and in vitro . Br. J. Cancer 1998 , 77 , 745 ; (b) Kashiyama , E. ; Hutchinson , I. ; Chua , M. S. ; Stinson , S. F. ; Phillips , L. R. ; Kaur , G. ; Sausville , E. A. ; Bradshaw , T. D. ; Westwell , A. D. ; Stevens , M. F. G. Antitumor benzothiazoles: Synthesis, metabolic formation, and biological properties of the C- and N-oxidation products of antitumor 2-(4-aminophenyl)benzothiazoles . J. Med. Chem. 1999 , 42 , 4172 – 4184 ; (c) Hutchinson , I. ; Chua , M. S. ; Browne , H. L. ; Trapani , V. ; Bradshaw , T. D. ; Westwell , A. D. ; Stevens , M. F. G. Antitumor benzothiazoles: Synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl)benzothiazoles . J. Med. Chem. 2001 , 44 , 1446 – 1455 .
   PubMed Web of Science ®Google Scholar
• (a) Lau , C. K. ; Dufresne , C. ; Gareau , Y. ; Zamboni , R. ; Labelle , M. ; Young , R. N. ; Metters , K. M. ; Rochette , C. ; Sawyer , N. ; Slipetz , D. M. ; Charette , L. ; Jones , T. ; McAuliffe , M. ; McFarlane , C. ; Ford-Hutchinson , A. W. Evalution of a series of non-quinoline leukotriene D4 receptor antagonist: Synthesis and sar of benzothiazoles and thiazoles substituted benzyl alcohols as potent LTD4 antagonists . Bioorg. Med. Chem. 1995 , 5 , 1615 – 1620 .
   Web of Science ®Google Scholar
• Bergman , J. M. ; Coleman , P. J. ; Cox , C. ; Hartman , G. D. ; Lindsley , C. ; Mercer , S. P. ; Roecker , A. J. ; Whitman , D. B. Praline bis-amide orexin receptor antagonists . PCT Int. Appl. 2006 , WO 2006127550 .
   Google Scholar
• Deligeorgiev , T. G. An improved method for the preparation of 2-aryl-, 2-hetaryl-, and 2-styrylbenzothiazoles . Dyes Pigments 1990 , 12 , 243 – 248 .
   Web of Science ®Google Scholar
• Hein , D. W. ; Alheim , R. J. ; Leavitt , J. J. The use of polyphosphoric acid in the synthesis of 2-aryl- and 2-alkyl-substituted benzimidazoles, benzoxazoles, and benzothiazoles . J. Ame. Chem. Soc. 1957 , 79 , 427 – 429 .
   Web of Science ®Google Scholar
• Kanaoka , Y. ; Hamada , T. ; Yonemitsu , O. Polyphosphate esters as a synthetic agent, XIII: Synthesis of 2-substituted benzoxazoles with PPA . Chem. Pharm. Bull. 1970 , 18 , 587 .
   Google Scholar
• Boger , D. L. A convenient preparation of 2-substituted benzothiazoles . J. Org. Chem. 1978 , 43 , 2296 – 2297 .
   Web of Science ®Google Scholar
• Hutchinson , I. ; Stevens , M. G. F. ; Westwell , A. D. The regiospecific synthesis of 5- and 7-monosubstituted and 5,6-disubstituted 2-arylbenzothiazoles . Tetrahedron Lett. 2000 , 41 , 425 – 428 .
   Web of Science ®Google Scholar
• Evindar , G. ; Batey , R. A. Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclization of ortho-halobenzanilides . J. Org. Chem. 2006 , 71 , 1802 – 1808 .
   PubMed Web of Science ®Google Scholar
• Perry , R. J. ; Wilson , B. D. Palladium-catalyzed syntheses of 2-arylbenzothiazoles. Organometallics 1994, 13, 3346–3350.
   Web of Science ®Google Scholar
• Tale , R. H. Novel synthesis of 2-arylbenzothiazoles mediated by ceric ammonium nitrate (CAN) . Org. Lett. 2002 , 4 , 1641 – 1642 .
   PubMed Web of Science ®Google Scholar
• Bose , D. S. ; Idrees , M. A convenient access to substituted benzothiazole scaffolds via intramolecular cyclization of thioformanilides . Tetrahedron Lett. 2007 , 48 , 669 – 672 .
   Web of Science ®Google Scholar
• (a) Sharghi , H. ; Shahsavari-Fard , Z. Al2O3/MeSO3H (AMA), a useful system for direct sulfonylation of phenols with p-toluenesulfonic acid . J. Iranian Chem. Soc. 2005 , 2 ( 1 ), 47 – 53 ; (b) Sharghi , H. ; Kaboudin , B. Alumina in methanesulfonic acid (AMA) as a new efficient reagent for direct acylation of phenol derivatives and Fries rearrangement: A convenient synthesis of o-hydroxyarylketones . J. Chem. Res. , 1998 , 628 – 629 ; (c) Sharghi , H. ; Hosseini Sarvari , M. One-step Beckmann rearrangement from carbonyl compounds and hydroxylamine hydrochloride in Al2O3/CH3SO3H (AMA) as a new reagent . J. Chem. Res. Synop. 2001 , 446 – 449 .
   Web of Science ®Google Scholar
• Mukhopadhyay , C. ; Datta , A. A green method for the synthesis of 2-arylbenzothiazoles . Heterocycles 2007 , 71 ( 8 ), 1837 – 1842 .
   Web of Science ®Google Scholar
• Kodomari , M. ; Tamaru , Y. ; Aoyama , T. Solvent-free synthesis of 2-aryl and 2-akylbenzothiazoles on silica gel under microwave irradiation . Synth. Commun. 2004 , 34 , 3029 .
   Web of Science ®Google Scholar