Examples of intramolecular cyclizations of functionalized diacetylenes are considered in the review. Cyclizations occur with the participation of one of the triple bonds that leads to ethynyl-substituted heterocycles, or of two triple bonds that is used in the synthesis of polycondensed heterocyclic systems and ensembles.
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References
R. D. Stephens and C. E. Castro, J. Org. Chem., 28, 3313 (1963).
F. Wessely and E. Zbiral, Justus Liebigs Ann. Chem., 605, 98 (1957).
S. Shvartsberg, S. F. Vasilevskii, and T. A. Prikhod'ko, Izv. Akad. Nauk SSSR, Ser. Khim., 2524 (1982).
R. C. Larock, in: F. Diederich, P. J. Stang, and R. R. Tykwinski (editors), Acetylene Chemistry, Wiley-VCH, Weinheim (2005), p. 51.
B. Godoi, R. F. Schumacher, and G. Zeni, Chem. Rev., 111, 2937 (2011).
I. Ueda, K. Miyawaki, T. Sugane, Y. Sakurai, Y. Wada, and M. Futai, Pharmazie, 55, 192 (2000).
D. Rodriguez, A. Navarro, L. Castedo, D. Dominguez, and C. Saa, Org. Lett., 2, 1497 (2000).
M. Rubina, M. Conley, and V. Gevorgyan, J. Am. Chem. Soc., 128, 5818 (2006).
I. A. Maretina and B. A. Trofimov, Adv. Heterocycl. Chem., 82, 157 (2002).
K. Shin and K. Ogasawara, Synlett, 859 (1995).
C. Koradin, W. Dohle, A. Rodriguez, B. Schmid, and P. Knochel, Tetrahedron, 59, 1571 (2003).
A. Arcadi, G. Bianchi, and F. Marinelli, Synthesis, 610 (2004).
G. W. Lee, N.-K. Kim, and K.-S. Jeong, Org. Lett., 12, 2634 (2010).
L. Capelli, P. Manini, A. Pezella, A. Napolitano, and M. d’Ischia, J. Org. Chem., 74, 7191 (2009).
U.-I. Kim, J. Suk, V. R. Naidu, and K.-S. Jeong, Chem. Eur. J., 14, 11406 (2008).
J.-Y. Lee, M.-H. Lee, and K.-S. Jeong, Supramol. Chem., 19, 257 (2007).
K.-J. Chang, M. K. Chae, C. Lee, J.-Y. Lee, and K.-S. Jeong, Tetrahedron Lett., 47, 6385 (2006).
K.-J. Chang, B.-N. Kang, M.-H. Lee, and K.-S. Jeong, J. Am. Chem. Soc., 127, 12214 (2005).
K.-J. Chang, D. Moon, M. S. Lah, and K.-S. Jeong, Angew. Chem., Int. Ed., 44, 7926 (2005).
M. Jacubert, O. Provot, J.-F. Peyrat, A. Hamze, J.-D. Brion, and M. Alami, Tetrahedron, 66, 3775 (2010).
S. Yamaguchi, C. Xu, H. Yamada, and A. Wakamiya, J. Organomet. Chem., 690, 5365 (2005).
C. Xu, A. Wakamiya, and S. Yamaguchi, Org. Lett., 6, 3707 (2004).
V. Fiandanese, D. Bottalico, G. Marchese, and A. Punzi, Tetrahedron, 64, 7301 (2008).
V. Fiandanese, D. Bottalico, G. Marchese, and A. Punzi, Tetrahedron, 64, 53 (2008).
V. Fiandanese, D. Bottalico, G. Marchese, A. Punzi, M. R. Quarta, and M. Fittipaldi, Synthesis, 3853 (2009).
Y. Liang, T. Meng, H.-J. Zhang, and Z. Xi, Synlett, 911 (2011).
A. Sniady, M. D. Sevilla, S. Meneni, T. Lis, S. Szafert, D. Khanduri, J. M. Finke, and R. Dembinski, Chem. Eur. J., 15, 7569 (2009).
N. Abe, Y. Harada, Y. Imachi, H. Fujii, A. Kakehi, and M. Shiro, Heterocycles, 72, 459 (2007).
G. Abbiati, A. Arcadi, E. Beccalli, G. Bianchi, F. Marinelli, and E. Rossi, Tetrahedron, 62, 3033 (2006).
T. Matsuda, S. Kadowaki, Y. Yamaguchi, and M. Murakami, J. Chem. Soc., Chem. Commun., 2744 (2008).
T. Okamoto, K. Kudoh, A. Wakamiya, and S. Yamaguchi, Org. Lett., 7, 5301 (2005).
S. Mehta and R. C. Larock, J. Org. Chem., 75, 1652 (2010).
J. Barluenga, M. Trincado, E. Rubio, and J. M. Gonzalez, Angew. Chem., Int. Ed., 42, 2406 (2003).
T. Okitsu, D. Nakazawa, R. Taniguchi, and A. Wada, Org. Lett., 10, 4967 (2008).
T. Yao and R. C. Larock, J. Org. Chem., 68, 5936 (2003).
M. Jacubert, A. Ticad, O. Provot, A. Hamze, J.-D. Brion, and M. Alami, Eur. J. Org. Chem., 4492 (2010).
S. Mehta, J. P. Waldo, and R. C. Larock, J. Org. Chem., 74, 1141 (2009).
N. A. Danilkina, S. Bräse, and I. A. Balova, Synlett, 517 (2011).
N. J. Kerrigan, in: J. J. Li (editor), Name Reactions for Carbocyclic Ring Formations, John Wiley and Sons, Hoboken, New Jersey (2010), p. 209.
F. Fringuelli and A. Taticchi, The Diels-Alder Reaction: Selected Practical Methods, John Wiley and Sons, Chichester (2001), p. 66.
N. Bushby, C. J. Moody, D. A. Riddick, and I. R. Waldron, J. Chem. Soc., Perkin Trans. 1, 2183 (2001).
M. Alajarin, B. Bonillo, A. Vidal, and D. Bautista, J. Org. Chem., 73, 291 (2008).
L. D. Shirtcliff, A. G. Hayes, M. M. Haley, F. Köhler, K. Hess, and R. Herges, J. Am. Chem. Soc., 128, 9711 (2006).
L. D. Shirtcliff, M. M. Haley, and R. Herges, J. Org. Chem., 72, 2411 (2007).
O. V. Vinogradova, V. N. Sorokoumov, and I. A. Balova, Tetrahedron Lett., 50, 6358 (2009).
S. F. Vasilevsky, E. V. Tretyakov, and H. D. Verkruijsse, Synth. Commun., 24, 1733 (1994).
O. V. Vinogradova, I. A. Balova, and V. V. Popik, J. Org. Chem., 76, 6937 (2011).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 100-111, January, 2012.
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Danilkina, N.A., Kulyashova, A.E. & Balova, I.A. Intramolecular cyclizations of functionalized diynes. Chem Heterocycl Comp 48, 95–106 (2012). https://doi.org/10.1007/s10593-012-0973-7
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DOI: https://doi.org/10.1007/s10593-012-0973-7