Abstract
Data on 1,3-dipolar cycloaddition of nitrones to free and coordinated nitriles producing 2,3-dihydro-1,2,4-oxadiazoles (or Δ4-1,2,4-oxadiazolines) are summarized. The latter compounds belong to the virtually unknown class of heterocyclic systems. The main factors responsible for the cycloaddition reactions are discussed. Particular attention is given to the role of metal centers in controlling the synthesis of 2,3-dihydro-1,2,4-oxadiazoles.
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References
T. L. Gilchrist, Heterocyclic Chemistry, Wiley, New York, 1992.
K. V. Gothelf and K. A. Jørgensen, Chem. Rev., 1998, 98, 863.
R. Huisgen, Angew. Chem., 1963, 75, 604.
K. B. G. Torssel, Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, Novel Strategies in Synthesis, Organic Nitro Chemistry, VCH Publishers, Inc, 1988.
H. M. I. Osborn, N. Gemmell, and L. M. Harwood, J. Chem. Soc., Perkin Trans. 1, 2002, 2419, and references therein.
K. V. Gothelf and K. A. Jørgensen, Chem. Commun., 2000, 1449.
J. P. Adams and J. R. Paterson, J. Chem. Soc., Perkin Trans. 1, 2000, 3695.
J. P. Adams and J. R. Paterson, J. Chem. Soc., Perkin Trans. 1, 1999, 749.
M. Frederickson, Tetrahedron, 1997, 53, 403.
Sk. Sahabuddin, A. Roy, M. G. B. Drew, B. G. Roy, B. Achari, and S. B. Mandal, J. Org. Chem., 2006, 71, 5980.
A. Chatterjee and P. K. Bhattacharya, J. Org. Chem., 2006, 71, 345.
A. Basak and S. C. Ghosh, Tetrahedron Lett., 2005, 46, 7385.
S. Moutel, M. Shipman, O. R. Martin, K. Ikeda, and N. Asano, Tetrahedron: Asymmetry, 2005, 16, 487.
J. Yu, J. DePue, and D. Kronenthal, Tetrahedron Lett., 2004, 45, 7247.
K. Singha, A. Roy, P. K. Dutta, S. Tripathi, S. Sahabuddin, B. Achari, and S. B. Mandal, J. Org. Chem., 2004, 69, 6507.
I. A. O’Neil, V. E. Ramos, G. L. Ellis, Ed Cleator, A. P. Chorlton, D. J. Tapolczay, and S. B. Kalindjian, Tetrahedron Lett., 2004, 45, 3659.
O. Tamura, T. Shiro, A. Toyao, and H. Ishibashi, Chem. Commun., 2003, 2678.
H. Ali Dondas, R. Grigg, S. Thibault, W. Anthony Thomas, and M. Thornton-Pett, Tetrahedron, 2002, 58, 5827.
T. Aftab, R. Grigg, M. Ladlow, V. Sridharan, and M. Thornton-Pett, Chem. Commun., 2002, 1754.
V. K. Aggarwal, S. J. Roseblade, J. K. Barrell, and R. Alexander, Org. Lett., 2002, 4, 1227.
Q. Zhao, F. Han, and D. L. Romero, J. Org. Chem., 2002, 67, 3317.
S. Kanemasa, N. Ueno, and M. Shirahase, Tetrahedron Lett., 2002, 43, 657.
J. D. White, P. R. Blakemore, E. A. Korf, and A. F. T. Yokochi, Org. Lett., 2001, 3, 413.
V. Ondrus, M. Orsag, L. Fisera, and N. Pronayova, Tetrahedron, 1999, 55, 10425.
M. Noguchi, H. Okada, S. Nishimura, Y. Yamagata, S. Takamura, M. Tanaka, A. Kakehi, and H. Yamamoto, J. Chem. Soc., Perkin Trans. 1, 1999, 185.
A. Arnone, G. Broggini, L. Bruche, G. Molteni, and G. Zecchi, J. Chem. Res. (S), 1998, 188.
K. Jensen, K. V. Gothelf, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 1997, 62, 2471.
P. de March, M. Figueredo, J. Font, S. Milan, A. Alvarez-Larena, J. F. Piniella, and E. Molins, Tetrahedron, 1997, 53, 2979.
U. Chicacchio, A. Rescifina, F. Casuscelli, A. Piperno, V. Pisani, and R. Romeo, Tetrahedron, 1996, 52, 14311.
A. Goti, F. Cardona, A. Brandi, S. Picasso, and P. Vogel, Tetrahedron: Asymmetry, 1996, 7, 1659.
G. Broggini, F. Folcio, N. Sardone, M. Sonzogni, and G. Zecchi, Tetrahedron: Asymmetry, 1996, 7, 797.
A. Arnone, L. Bruche, L. Baranti, and G. Zecchi, J. Chem. Res. (S), 1995, 282.
U. Chiacchio, G. Buemi, F. Casuscelli, A. Procopio, A. Rescifina, and R. Romeo, Tetrahedron, 1994, 50, 5503.
P. J. Smith, D. J. Soose, and C. S. Wilcox, J. Am. Chem. Soc., 1991, 113, 7412.
D. M. Tschaen, R. R. Whittle, and S. M. Weinreb, J. Org. Chem., 1986, 51, 2604.
P. DeShong and J. M. Leginus, J. Am. Chem. Soc., 1983, 105, 1686.
A. Padwa, K. Koehler, and A. Rodriguez, J. Am. Chem. Soc., 1981, 103, 4974.
P. Merino, Science of Synthesis, 2004, 27, 511 and references therein.
E. N. Zil’berman, Reaktsii nitrilov [Reactions of Nitriles], Khimiya, Moscow, 1972 (in Russian).
V. Yu. Kukushkin and A. J. L. Pombeiro, Chem. Rev., 2002, 102, 1771.
Y. R. Do, S. Ch. Nam, K. K. Sung, S. Ch. Eun, and H. S. Il, J. Chem. Soc., Perkin Trans. 2, 1999, 81.
W. Szczepankiewicz, J. Suwinski, and Z. Karczmarzyk, Khim. Geterotsikl. Soedin., 2004, 932 [Chem. Heterocycl. Compd., 2004, 40, 801 (Engl. Transl.)].
C. Balsamini, G. Spadoni, A. Bedini, G. Tarzia, M. Lanfranchi, and M. A. Pellinghelli, J. Heterocycl. Chem., 1992, 29, 1593.
M. Fred, J. Heterocycl. Chem., 1972, 9, 739.
R. Huisgen, W. Mack, and K. Bast, Pat. DE 19610728; Chem. Abstrs, 1964, 61, 47917.
V. G. Andrianov, E. N. Rozhkov, and A. V. Eremeev, Khim. Geterotsikl. Soedin., 1991, 262 [Chem. Heterocycl. Compd., 1991 (Engl. Transl.)].
J. Azizian, M. Madani, and S. Souzangarzadeh, Synth. Commun., 2005, 35, 765.
R. M. Srivastava, Quimica Nova, 1995, 18, 303.
M. R. Manrao, K. K. Gill, J. R. Sharma, and P. S. Kalsi, Indian J. Heterocycl. Chem., 1995, 5, 151.
D. B. Repke, H. P. Albrecht, and J. G. Moffatt, J. Org. Chem., 1975, 40, 2481.
R. M. Srivastava, M. F. Rosa, C. Eduardo, M. Carvalho, S. da G. M. Portugal, I. M. Brinn, M. Da Conceicao Pereira, and O. A. C. Antunes, Heterocycles, 2000, 53, 191.
F. M. Pallos, J. R. DeBaun, and A. D. Gutman, Pat. US 75-632603; Chem. Abstrs, 1976, 85, 104204.
J. A. Claisse, G. I. Gregory, and W. K. Warburton, Pat. GB 1228142 (A); Chem. Abstrs, 1970, 72, 21696.
C. P. Singh and H. Hasan, J. Indian Council of Chemists, 2002, 19, 46.
M. R. G. Manrao, K. Karamjit, J. R. Sharma, and P. S. Kalsi, Indian J. Heterocycl. Chem., 1995, 5, 151.
A. Chimirri, S. Grasso, A.-M. Montforte, A. Rao, and M. Zappala, Farmaco, 1996, 51, 125.
J. Sterne, S. Le Guilcher, and M. Rousselet, Therapie, 1972, 27, 517.
F. Lauria, V. Vecchietti, and G. Tosolini, Gazz. Chim. Ital., 1964, 94, 478.
J. Sterne and C. Hirsch, Therapie, 1965, 20, 89.
J. M. D. Aron-Samuel, 1965, Pat. FR 19640424; Chem. Abstrs, 1965, 63, 63149.
L. Eberson, J. J. McCullough, Ch. M. Hartshorn, and M. P. Hartshorn, J. Chem. Soc., Perkin Trans. 2, 1998, 41.
Y. Yu, N. Watanabe, M. Ohno, and S. Eguchi, J. Chem. Soc., Perkin Trans. 1, 1995, 1417.
Y. Yu, M. Ohno, and S. Eguchi, J. Chem. Soc., Chem. Commun., 1994, 331.
Y. Yu, H. Fujita, M. Ohno, and S. Eguchi, Synthesis, 1995, 498.
R. Plate, P. H. H. Hermkens, J. M. M. Smits, R. J. F. Nivard, and H. C. J. Ottenheijm, J. Org. Chem., 1987, 52, 1047.
R. Sustmann, Tetrahedron Lett., 1971, 2717.
R. Sustmann, Tetrahedron Lett., 1971, 2721.
M. L. Kuznetsov and V. Yu. Kukushkin, J. Org. Chem., 2006, 71, 582.
M. L. Kuznetsov, V. Yu. Kukushkin, A. I. Dement’ev, and A. J. L. Pombeiro, J. Phys. Chem. A, 2003, 107, 6108.
P. H. H. Hermkens, J. H. v. Maarseveen, C. G. Kruse, and H. W. Scheeren, Tetrahedron, 1988, 44, 6491.
V. D. Kiselev, G. G. Iskhakova, E. A. Kashaeva, M. S. Shikhab, M. D. Medvedeva, and A. I. Konovalov, Zh. Obshch. Khim., 2003, 73, 1884 [Russ. J. Gen. Chem., 2003, 73 (Engl. Transl.)].
A. Díaz-Ortiz, E. Díez-Barra, A. de la Hoz, A. Moreno, M. J. Gómez-Escalonilla, and A. Loupy, Heterocycles, 1996, 43, 1021.
G. Broggini, G. Molteni, A. Terraneo, and G. Zecchi, Heterocycles, 2003, 59, 823 and references cited therein.
M. A. J. Charmier, V. Yu. Kukushkin, and A. J. L. Pombeiro, J. Chem. Soc., Dalton Trans., 2003, 2540.
N. A. Bokach, A. A. Krokhin, A. A. Nazarov, V. Yu. Kukushkin, M. Haukka, J. J. R. Fraústo da Silva, and A. J. L. Pombeiro, Eur. J. Inorg. Chem, 2005, 3042.
B. Desai, T. N. Danks, and G. Wagner, J. Chem. Soc., Dalton Trans., 2003, 2544.
B. Desai, T. N. Danks, and G. Wagner, Dalton Trans, 2004, 166.
G. Wagner, A. J. L. Pombeiro, and V. Yu. Kukushkin, J. Am. Chem. Soc., 2000, 122, 3106.
G. Wagner, M. Haukka, J. J. R. Fraústo da Silva, A. J. L. Pombeiro, and V. Yu. Kukushkin, Inorg. Chem., 2001, 40, 264.
G. Wagner, Inorg. Chim. Acta, 2004, 357, 1320.
G. Wagner, Chem. Eur. J., 2003, 9, 1503.
G. Wagner and M. Haukka, J. Chem. Soc., Dalton Trans., 2001, 2690.
M. A. J. Charmier, M. Haukka, and A. J. L. Pombeiro, Dalton Trans, 2004, 2741.
V. Yu. Kukushkin, A. J. L. Pombeiro, J. J. R. Fraústo da Silva, and G. Wagner, Pat. WO 2001098283; Chem. Abstrs, 2001, 136, 53750.
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Dedicated to Academician O. M. Nefedov on the occasion of his 75th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1803–1815, November, 2006.
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Bokach, N.A., Kukushkin, V.Y. 1,3-dipolar cycloaddition of nitrones to free and coordinated nitriles: Routes to control the synthesis of 2,3-dihydro-1,2,4-oxadiazoles. Russ Chem Bull 55, 1869–1882 (2006). https://doi.org/10.1007/s11172-006-0528-0
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DOI: https://doi.org/10.1007/s11172-006-0528-0