Alkyne [3 + 2] cycloadditions of iodosydnones toward functionalized 1,3,5-trisubstituted pyrazoles

Journal of Organic Chemistry

Volumn 75, Issue 3, 2010, Pages 984-987

  Browne, Duncan L ^a   Taylor, John B ^b   Plant, Andrew ^b,c   Harrity, Joseph P A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

^c JEALOTT S HILL RESEARCH STATION   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; CYCLOADDITIONS; FUNCTIONALIZED; HETEROATOM BONDS; PYRAZOLES; REGIOCONTROL; TERMINAL ALKYNE;

CYCLOADDITION;

ACETYLENE;

1,3 DIPHENYL 5 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL) 1H PYRAZOLE; 4 IODOSYDNONE DERIVATIVE; 5 IODO 1 (4 NITROPHENYL) 3 PHENYL 1H PYRAZOLE; ALKYNE; ALKYNE DERIVATIVE; PYRAZOLE DERIVATIVE; SYDNONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLOADDITION; REACTION TIME; SUBSTITUTION REACTION; SYNTHESIS;

EID: 75749084018     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902514v     Document Type: Article

References (25)

1. (a) Elguero, J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; vol. 3, p 1.
2. (b) Lamberth, C. Heterocycles 2007, 71, 1467.
3. (c) Singh, P.; Paul, K.; Holzer,W. Bioorg. Med. Chem. 2006, 14, 5061 and references cited therein.
4. (a) Trofimenko, S. Prog. Inorg. Chem. 1986, 34, 115.
5. (b) Danel, A.; He, Z.; Milburn, G. H. W.; Tomasik, P. J. Mat. Chem. 1999, 9, 339.
6. Heterocyclic Chemistry; Joule, J.A., Mills, K., Eds.; Blackwell Science: Oxford, 2000.
7. (a) Li, H.; Wang, Y.; McMillen, W. T.; Chatterjee, A.; Toth, J. E.; Mundla, S. R.; Voss, M.; Boyer, R. D.; Sawyer, J. S. Tetrahedron 2007, 63, 11763.
8. (b) Grimmett, M. R.; Iddon, B. Heterocycles 1994, 37, 2087.
9. (a) McLaughlin, M.; Marcantonio, K.; Chen, C.-y.; Davies, I. W. J. Org. Chem. 2008, 73, 4309.
10. (b) Goikhman, R.; Jacques, T. L.; Sames, D. J. Am. Chem. Soc. 2009, 131, 3042.
11. (a) Browne, D. L.; Helm, M. D.; Plant, A.; Harrity, J. P. A. Angew. Chem., Int. Ed. 2007, 46, 8656.
12. (b) Browne, D. L.; Taylor, J. B.; Plant, A.; Harrity, J. P. A. J. Org. Chem. 2009, 74, 396.
13. (c) Browne, D. L.; Vivat, J. F.; Plant, A.; Gomez-Bengoa, E.; Harrity, J. P. A. J. Am. Chem. Soc. 2009, 131, 7762.
14. Boronic Acids; Hall, D.G., Ed.; Wiley-VCH: Weinheim, 2005.
15. Dickopp, H. Chem. Ber. 1974, 107, 3036.
16. Dumitras-cu, F.; Mitan, C. I.; Dumitrescu, D.; Drǎghici, C.; Cǎproiu, M. T. ARKIVOC 2002, 2, 80.
17. Jiang, Q.; Ryan, M.; Zhichkin, P. J. Org. Chem. 2007, 72, 6618.
18. Terminal alkynes were reported to undergo cycloaddition with excellent regiocontrol by Huisgen in his seminal report of this chemistry: Huisgen, R.; Grashey, R. Angew. Chem., Int. Ed. Engl. 1962, 1, 48.
19. Pyrazoles 8, 14, 18, underwent cross-coupling with a selection of boronic acids in yields of > 79%. Details of these reactions can be found in the Supporting Information.
20. Palladium mediated amination reactions: (a) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
21. (b) For a discussion of the challenges associated with Pd-catalyzed amination of iodoarenes, see: Fors, B. P.; Davis, N. R.; Buchwald, S. L. J. Org. Chem. 2009, 131, 5766. Copper mediated amination reactions:
22. (c) Xia, N.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 337.
23. (d) Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742.
24. Lithiation of pyrazole 12 followed by quenching with PhSSPh provided the corresponding sulfide in low yield as an impure product. We speculate that lithiation of this pyrazole is complicated by side reactions at the N-p-nitrophenyl group.
25. Tao, C.-Z.; Cui, X.; Li, J.; Liu, A.-X.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2007, 48, 3525.