Niobium Pentachloride Promoted Conversion of Carboxylic Acids to Carboxamides­: Synthesis of the 4-Aryl-1,2,3,4-tetrahydroisoquinoline Alkaloid­ Structures

 

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Abstract

A practical method for the conversion of carboxylic acids to the corresponding carboxamides mediated by niobium pentachloride under mild conditions is described. The synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures was accomplished via benzylic lithiation of N-methyl-3,4-dimethoxy-2-(4′-methoxybenzyl)benzamide.

References

• 1 Humphrey JM. Chamberlin AR. Chem. Rev.  1997,  97:  2243 
  CrossrefPubMedGoogle Scholar
• 2 Herrero S. Lopez MTG. Latorre M. Cenarruzabeitia E. Del Rio J. Herranz R. J. Org. Chem.  2002,  67:  3866 
  CrossrefGoogle Scholar
• 3a Mitchell JA. Reid EE. J. Am. Chem. Soc.  1931,  53:  1879 
  CrossrefGoogle Scholar
• 3b Ruhoff JR. Reid EE. J. Am. Chem. Soc.  1937,  59:  401 
  CrossrefGoogle Scholar
• 4 Wagner RB. inventors; U.S. Patent  2932665. 
• 5 Cartwright CR. inventors; U.S. Patent  2916514. 
• 6 Frederick G, and Stryk V. inventors; Can. Patent  716609. 
• 7a Larock RC. In Comprehensive Organic Transformations   VCH Publishers; New York: 1989.  p.972-976  
  Google Scholar
• 7b Beak P. Brown RA. J. Org. Chem.  1982,  47:  34 
  Google Scholar
• 7c Khaldi M. Chrétien F. Chapleur Y. Bull. Soc. Chim. Fr.  1996,  133:  7 
  Google Scholar
• 7d Lynn JW. English J. J. Am. Chem. Soc.  1951,  73:  4284 
  Google Scholar
• 7e Snyder HR. Putnam RE. J. Am. Chem. Soc.  1954,  76:  33 
  Google Scholar
• 7f McCabe ET. Barthel WF. Gertler SI. Hall SA. J. Org. Chem.  1954,  45:  2750 
  Google Scholar
• 7g Hauser CR. Walker HG. J. Am. Chem. Soc.  1947,  69:  295 
  Google Scholar
• 7h Suryanarayama MVS. Pandey KS. Shiri P. Raghuveeran CD. Dangi RS. Swamy RV. Rao KM. J. Pharm. Sci.  1991,  80:  1055 
  Google Scholar
• 8 Tanabe K. Okazaki S. Appl. Catal., A  1995,  133:  191 
  Google Scholar
• 10 Heathcock CH. Lopes RSC. Lopes CC. Tetrahedron Lett.  1992,  33:  6775 
  CrossrefGoogle Scholar
• 11 Kalinin AV. Silva AJM. Lopes CC. Lopes RSC. Snieckus V. Tetrahedron Lett.  1998,  39:  4995 
  CrossrefGoogle Scholar
• 12a Ooi BL. Xu QY. Shibahara T. Inorg. Chim. Acta  1998,  274:  103 
  Google Scholar
• 12b Roy CN. Trivedi SRC. J. Indian Chem. Soc.  1981,  58:  1036 
  Google Scholar
• 13a Avery MA. Verlander MS. Goodman M. J. Org. Chem.  1980,  45:  2750 
  CrossrefGoogle Scholar
• 13b Reitz A. Avery MA. Verlander MS. Goodman M. J. Org. Chem.  1981,  46:  4859 
  CrossrefGoogle Scholar
• 14 Schreier E. Helv. Chim. Acta  1964,  47:  1529 
  CrossrefGoogle Scholar
• 15 Wilson JD. Weingarten H. Can. J. Chem.  1970,  48:  983 
  CrossrefGoogle Scholar
• 16 Brown DA. Wallbridge MGH. Alcock NW. J. Chem. Soc., Dalton Trans.  1993,  2037 
  CrossrefGoogle Scholar
• 17 Kapoor R. Sharma R. Kapoor P. Indian J. Chem., Sect. A  1985,  24:  761 
  Google Scholar
• 18a Kobayashi S. Tokumoto T. Taira Z. J. Chem. Soc., Chem. Commun.  1984,  1043 
  CrossrefGoogle Scholar
• 18b Kohli JD. Goldberg LI. J. Pharm. Pharmacol.  1980,  32:  225 
  CrossrefGoogle Scholar
• 18c Jacob JN. Nichols DE. Kohli JD. Glock D. J. Med. Chem.  1981,  24:  1013 
  CrossrefGoogle Scholar
• 19a Costa PRR. Lopes CC. Lopes RSC. Marinho MFG. Castro RN. Synth. Commun.  1988,  14:  1723 
  Google Scholar
• 19b Lopes CC. Lima ELS. Silva AJM. Costa PRR. Synth. Commun.  1988,  14:  1731 
  Google Scholar
• 20 Gore VG. Narasimhan NS. J. Chem. Soc., Perkin Trans. 1  1988,  481 
  CrossrefGoogle Scholar
• 21 Brossi A. Grethe G. Teitel S. J. Org. Chem.  1970,  35:  1100 
  CrossrefGoogle Scholar

Niobium pentachloride with purity >99% was a gift kindly provided by the Brazilian Company of Metallurgy and Mines (CBMM) Araxá city Minas Gerais state Brazil.