A Novel Method for the Synthesis of 2(3H)‐Benzimidazolones, 2(3H)‐Benzoxazolone, and 2(3H)‐Benzothiazolone via In Situ Generated Ortho Substituted Benzoic Acid Azides: Application of Ammonium Azide and Vilsmeier Complex for Acid Azide Generation

References

• Patai , S. 1971 . The Chemistry of the Azido Group 301 New York : Interscience Publishers .
   Google Scholar
• Smith , P. A.S. 1946 . Org. Reactions , 3 : 337
   Google Scholar
• Sridhar , R. and Perumal , P. T. 2003 . Synthesis of acyl azides using Vilsmeier Complex . Synth. Commun. , 33 : 607 [CROSSREF]
   Web of Science ®Google Scholar
• Majo , V. J. and Perumal , P. T. 1998 . The intramolecular electrophilic substitution of azides by iminium species. A convenient and novel method for the construction of nitrogen heterocycles by cyclisation under Vilsmeier conditions . J. Org. Chem. , 63 : 7136 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Majo , V. J. and Perumal , P. T. 1996 . One‐pot synthesis of heterocyclic β‐chlorovinyl aldehydes using Vilsmeier reagent . J. Org. Chem. , 61 : 6523 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Majo , V. J. and Perumal , P. T. 1997 . The Vilsmeier cyclisation of azides. Synthesis oxazoles and vinyl azides from 2‐azidoacetophenones . Tetrahedron Lett. , 38 : 6889 [CROSSREF]
   Web of Science ®Google Scholar
• Woolley , D. W. 1944 . Some biological effects produced by benzimidazole and their reversal by purines . J. Biol. Chem. , 152 : 225
   Google Scholar
• Brink , N. G. and Folkers , K. G. 1952 . The degradation of vitamin B12 to 1‐α‐D‐ribofuranosyl‐5,6‐dimethyl benzimidazole . J. Am. Chem. Soc. , 74 : 2856
   Google Scholar
• Wright , J. B. 1951 . Chemistry of the benzimidazoles . Chem. Rev. , 48 : 520
   Google Scholar
• Lespagnol , A. and Lefebvre , M. 1945 . Hypnotic effect of benzoxazolone substitutes . Bull. Soc. Chim. , 12 : 386
   PubMedGoogle Scholar
• Gokhan , N. , Erdog¢an , H. , Durlu , N. T. and Demirdamar , R. 1999 . Analgesic activity of acylated 2‐benzoxazolinone derivatives . Il Farmaco , 54 : 112 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMedGoogle Scholar
• Ucar , H. , Van derpoorten , K. , Cacciaguerra , S. , Spampinato , S. , Stables , J. P. , Depovere , P. , Isa , M. , Masereel , B. , Delarge , J. and Poupaert , J. H. 1998 . Synthesis and anticonvulsant activity of 2(3H)‐benzoxazolone and 2(3H)‐benzothiazolone derivatives . J. Med. Chem. , 41 : 1138 [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Prakash , O. , Batra , H. , Kaur , H. , Sharma , P. K. , Sharma , V. , Singh , S. P. and Moriarty , R. M. 2001 . Hypervalent iodine oxidative rearrangement of anthrailamides, salicylamides and some β‐substituted amides: a new and convenient synthesis of 2‐benzimidazolones, 2‐benoxazolones and related compounds . Synthesis , 4 : 541 [CROSSREF]
   Google Scholar
• Wright , J. B. 1951 . Chemistry of the benzimidazoles . Chem. Rev. , 48 : 446
   Google Scholar
• Scott , A. W. and Mote , J. H. 1927 . The Beckmann rearrangement of salicylhydroxamic acid derivatives . J. Am. Chem. Soc. , 49 : 2545
   Google Scholar
• Mills , W. H. and Whitworth , J. B. 1927 . The condensation of o‐aminothiophenol with αβ‐unsaturated acids . J. Chem. Soc. , : 2738 [CROSSREF]
   Google Scholar
• Rodd , E. H. 1951 . Chemistry of Carbon Compounds Vol. IV A , 330 Elsevier Publishing Company .
   Google Scholar
• Elderfield , R. C. 1957 . Heterocyclic Compounds Vol. 5 , 284 New York : John Wiley & Sons .
   Google Scholar
• Brown , M. and Benson , R. E. 1966 . Cyanovinyltetrazoles . J. Org. Chem. , 31 : 3849
   Google Scholar
• Curtius , T. and Heidenreich , K. 1895 . Hydrazides and azides of organic acids . J. Prakt. Chem. , 52 : 454
   Google Scholar
• Finnegan , W. G. , Henry , R. A. and Lofquist , R. J. 1958 . An improved synthesis of 5‐substituted tetrazoles . Am. Chem. Soc. , 80 : 3908
   Web of Science ®Google Scholar
• Majo , V. J. and Perumal , P. T. 1996 . Dimerization of 2‐aminobenzoic acids under Vilsmeier conditions: A novel route to the synthesis of 4‐(3H)‐quinazolinones . Tetrahedron Lett. , 37 : 5015 [CROSSREF]
   Web of Science ®Google Scholar
• Aldrich Catalog Handbook of Fine Chemicals 2000–2001 917 Sigma‐Aldrich Co. . H1,985–9
   Google Scholar
• Aldrich Catalog Handbook of Fine Chemicals 2000–2001 160 Sigma‐Aldrich Co. . 15705‐8
   Google Scholar
• Aldrich Catalog Handbook of Fine Chemicals 2000–2001 918 Sigma‐Aldrich Co. . 40760‐7
   Google Scholar
• Wright , W. B. 1965 . N,N′‐carbonyldiimidazole as a reagent for the preparation of five‐membered heterocycles . J. Heterocycl. Chem. , 2 : 41
   Google Scholar
• Smalley , R. K. and Stocker , A. W. 1984 . The base‐induced decomposition of ethyl N‐(o‐azidoaryl) carbamates. An unexpected formation of azo‐compounds . Tetrahedron Lett. , 25 : 1389 [CROSSREF]
   Google Scholar
• Kym , O. and Ratner , L. 1912 . Substituted α‐hydroxy‐ and α‐methylbenzimidazoles . Ber. , 45 : 3238
   Google Scholar