(Arylsulfonyl)acetones and -acetonitriles: New Activated Methylenic Building Blocks for Synthesis of 1,2,3-Triazoles

Abstract

β-Keto sulfones and β-nitrile sulfones were used as building blocks for 1,2,3-triazole synthesis in the Dimroth cyclization. It was shown, that sulfone reagents undergo base-catalyzed cyclization under mild conditions (at room temperature) to give 1,2,3-triazoles in moderate to excellent yields. This fact has confirmed the high nucleophilicity of sulfonylmethylenic compounds and allows new synthetic applications.

Key words

azides - triazoles - sulfones - Dimroth reaction

References

• 1 Terrett NK. Combinatorial Chemistry   Oxford University Press; New York: 1998. 
• 2 McMahon JB. Gulakowsky RJ. Weislow OS. Schultz RJ. Narayanan VL. Clanton DJ. Pedemonte R. Wassmundt FW. Buckheit RW. Decker WD. White EL. Bader JP. Boyd MR. Antimicrob. Agents Chemother.  1993,  37:  754 
• 3 Williams TM. Ciccarone TM. Mac Tough SC. Rooney CS. Balani SK. Condra JH. Emini EA. Goldman ME. Greenlee WJ. Kauffman LR. O’Brien JA. Sardana VV. Schleif WA. Theoharides AD. Anderson PS. J. Med. Chem.  1993,  36:  1291 
• 4 Young SD. Amblard MC. Britcher SF. Grey VE. Tran LO. Lumma WC. Huff JR. Schleif WA. Emini EE. O’Brien JA. Pettibone DJ. Bioorg. Med. Chem. Lett.  1995,  5:  491 
• 5 Artico M. Silvestri R. Stefancich G. Massa SR. Pagnozzi E. Musiu E. Scintu E. Pinna E. Tinti P. La Colla P. Arch. Pharm. (Weinheim, Ger.)  1995,  328:  223 
• 6 Artico M. Silvestri R. Massa S. Loi AG. Corrias S. Piras G. La Colla P. J. Med. Chem.  1996,  39:  522 
• 7 Silvestri R. De Martino G. La Regina G. Artico M. Massa S. Vargiu L. Mura M. Loi AG. Marceddu T. La Colla P. J. Med. Chem.  2003,  46:  2482 
• 8 Ragno R. Artico M. De Martino G. La Regina G. Coluccia A. Di Pasquali A. Silvestri R. J. Med. Chem.  2005,  48:  213 
• 9 Krivopalov VP. Shkurko OP. Russ. Chem. Rev. (Engl. Transl.)  2005,  74:  339 
• 10 Wamhoff H. Wambach W. Chem.-Ztg.  1989,  113:  11 
• 11 Davies HML. Cantrell WR. Romines KR. Baum JS. Org. Synth.  1992,  70:  93 
• 12 Hughes CC. Kennedy-Smith JJ. Trauner D. Org. Lett.  2003,  5:  4113 
• 13 Smith PAS. Boyer JH. Org. Synth.  1951,  31:  14 
• 14 Hoffman RV. Org. Synth.  1981,  60:  121 
• 15 Tietze LF. Eicher T. Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium   Georg Thieme Verlag; Stuttgart: 1991.  p.511 
• 16 Tavares DF. O’Sullivan WI. Hauser CR. J. Org. Chem.  1962,  27:  1251