Multicomponent heterocyclization reactions with controlled selectivity (Review)

S. L. Schreiber, Science, 287, 1964 (2000).

B. M. Trost, Acc. Chem. Res., 35, 695 (2002).

P. A. Wender, G. G. Gamber, R. D. Hubbard, S. M. Pham, and L. Zhang, J. Am. Chem. Soc., 127, 2836 (2005).

P. A. Wender, S. T. Handy, and D. L. Wright, Chem. Ind., 765 (1997).

E. Ruijter, R. Scheffelaar, and R. V. A. Orru, Ang. Chem., Int. Ed., 50, 6234 (2011).

J. E. Biggs-Houck, A. Younai, and J. T. Shaw, Curr. Opin. Chem. Biol., 14, 371 (2010).

F. Sha and X. Huang, Angew. Chem., Int. Ed., 48, 3458 (2009).

Y. Suzuki, Y. Ohta, S. Oishi, N. Fujii, and H. Ohno, J. Org. Chem., 74, 4246 (2009).

N. Isambert and R. Lavilla, Chem.–Eur. J., 14, 8444 (2008).

A. Kruithof, E. Ruijter, and R. V. A. Orru, Curr. Org. Chem., 15, 204 (2011).

V. A. Chebanov, K. A. Gura, and S. M. Desenko, Top. Heterocycl. Chem., 23, 41 (2010).

S. M. Desenko, V. D. Orlov, N. V. Getmanskii, O. V. Shishkin, S. V. Lindeman, and Yu. T. Struchkov, Khim. Geterotsikl. Soedin., 481 (1993). [Chem. Heterocycl. Compd., 29, 406 (1993)].

K. Wermann and M. Hartmann, Synthesis, 189 (1991).

A. T. Khan and M. M. Khan, Tetrahedron Lett., 52, 3455 (2011).

I. Drizin, M. W. Holladay, L. Yi, H. Q. Zhang, S. Gopalakrishnan, M. Gopalakrishnan, K. L. Whiteaker, S. A. Buckner, J. P. Sullivan, and W. A. Carroll, Bioorg. Med. Chem. Lett., 12, 1481 (2002).

V. A. Chebanov, V. E. Saraev, S. M. Desenko, V. N. Chernenko, I. V. Knyazeva, U. Groth, T. N. Glasnov, and C. O. Kappe, J. Org. Chem., 73, 5110 (2008).

V. A. Chebanov, Ya. I. Sakhno, S. M. Desenko, S. V. Shishkina, V. I. Musatov, O. V. Shishkin, and I. V. Knyazeva, Synthesis, 2597 (2005).

Q. Chen, L.-L. Jiang, C.-N. Chen, and G.-F. Yang, J. Heterocycl. Chem., 46, 139 (2009).

M. P. Sibi and M. Liu, Curr. Org. Chem., 5, 719 (2001).

S. P. Flanagan and P. J. Guiry, J. Organomet. Chem., 691, 2125 (2006).

G. Zanoni, F. Castronovo, M. Franzini, G. Vidari, and E. Giannini, Chem. Soc. Rev., 32, 115 (2003).

D. Bonne, Y. Coquerel, T. Constantieux, and J. Rodriguez, Tetrahedron: Asymmetry, 21, 1085 (2010).

G. Guillena, D. J. Ramón, and M. Yus, Tetrahedron: Asymmetry, 18, 693 (2007).

A.-N. Alba, X. Companyo, M. Viciano, and R. Rios, Curr. Org. Chem., 13, 1432 (2009).

R. Wohlgemuth, Curr. Opin. Biotechnol., 21, 713 (2010).

M. A. Kolosov, V. D. Orlov, D. A. Beloborodov, and V. V. Dotsenko, Mol. Diversity, 13, 5 (2009).

D. M. D’Souza and T. J. J. Müller, Chem. Soc. Rev., 36, 1095 (2007).

N. Isambert, M. del Mar Sanchez Duque, J.-C. Plaquevent, Y. Génisson, J. Rodriguez, and T. Constantieux, Chem. Soc. Rev., 40, 1347 (2011).

J. B. Bariwal, J. C. Trivedi, and E. V. van der Eycken, Top. Heterocycl. Chem., 25, 169 (2010).

S. Caddick and R. Fitzmaurice, Tetrahedron, 65, 3325 (2009).

M. C. Bagley and M. Caterina Lubinu, Top. Heterocycl. Chem., 1, 31 (2006).

C. O. Kappe, Angew. Chem. Int. Ed., 43, 6250 (2004).

W. Bonrath and R. Schmidt, in: Advances in Organic Synthesis, Science, Bentham (2005), p. 81.

R. Cella and H. A. Stefani, Tetrahedron, 65, 2619 (2009).

V. V. Lipson, V. D. Orlov, S. M. Desenko, T. M. Karnozhitskaya, and M. G. Shirobokova, Khim. Geterotsikl. Soedin., 664 (1999). [Chem. Heterocycl. Compd., 35, 595 (1999)].

V. V. Lipson, V. V. Borodina, and M. G. Shirobokova, Ukr. Khim. Zh., 71, 95 (2005).

V. V. Lipson, S. M. Desenko, V. V. Borodina, M. G. Shirobokova, T. M. Karnozhitskaya, V. I. Musatov, and S. V. Kravchenko, Khim. Geterotsikl. Soedin., 246, (2005). [Chem. Heterocycl. Compd., 41, 216 (2005)].

V. V. Lipson, V. V. Borodina, and V. I. Musatov, Zh. Org. Farm. Khim., 4, No. 1, 62 (2006).

V. V. Lipson, V. D. Orlov, S. M. Desenko, S. V. Shishkina, O. V. Shishkin, and M. G. Shirobokova, Khim. Geterotsikl. Soedin., 1190 (2000). [Chem. Heterocycl. Compd., 36, 1039 (2000)].

V. V. Lipson, S. M. Desenko, M. G. Shirobokova, O. V. Shishkin, and S. V. Shishkina, Zh. Org. Khim., 42, 1040 (2006).

S. Tu., C. Li, F. Shi, D. Zhou, Q. Shao, L. Cao, and B. Jiang, Synthesis, 369 (2008).

S.-L. Wang, Y.-P. Liu, B.-H. Xu, X.-H. Wang, B. Liang, and S.-J. Tu, Tetrahedron, 67, 9417 (2011).

S. M. Desenko, V. D. Orlov, N. V. Getmanskii, O. V. Shishkin, S. V. Lindeman, and Yu. T. Struchkov, Dokl. Akad. Nauk SSSR, 324, 801 (1992).

S. Tu, B. Jiang, Y. Zhang, R. Jia, J. Zhang, C. Yao, and F. Shi, Org. Biomol. Chem., 5, 355 (2007).

D. Tejedor and F. Garcia-Tellado, Chem. Soc. Rev., 36, 484 (2007).

N. Elders, E. Ruijter, F. J. J. de Kanter, M. B. Groen, and R. V. A. Orru, Chem.–Eur. J., 14, 4961 (2008).

F. A. Carey and R. J. Sundberg, in: Advanced Organic Chemistry. Part A: Structure and Mechanisms, Springer, New York (2007), p. 285.

A. Loupy (editor), Microwaves in Organic Synthesis, 2nd ed., Wiley, Weinheim (2006).

A. de la Hoz, A. Díaz-Ortiz, and A. Moreno, Curr. Org. Chem., 8, 903 (2004).

A. de la Hoz, M. P. Prieto, M. Rajzmann, A. de Cózar, A. Díaz-Ortiz, A. Moreno, and F. P. Cossío, Tetrahedron, 64, 8169 (2008).

T. Razzaq, J. M. Kremsner, and C. O. Kappe, J. Org. Chem., 73, 6321 (2008).

M. A. Herrero, J. M. Kremsner, and C. O. Kappe, J. Org. Chem., 73, 36 (2008).

V. A. Chebanov, E. A. Muravyova, S. M. Desenko, V. I. Musatov, I. V. Knyazeva, S. V. Shishkina, O. V. Shishkin, and C. O. Kappe, J. Comb. Chem., 8, 427 (2006).

E. A. Muravyova, S. M. Desenko, R. V. Rudenko, S. V. Shishkina, O. V. Shishkin, Yu. V. Sen'ko, E. V. Vashchenko, and V. A. Chebanov, Tetrahedron, 67, 9389 (2011).

V. A. Chebanov, Ya. I. Sakhno, S. M. Desenko, V. N. Chernenko, V. I. Musatov, S. V. Shishkina, O. V. Shishkin, and C. O. Kappe, Tetrahedron, 63, 1229 (2007).

Ya. I. Sakhno, S. M. Desenko, S. V. Shishkina, O. V. Shishkin, D. O. Sysoyev, U. Groth, C. O. Kappe, and V. A. Chebanov, Tetrahedron, 64, 11041 (2008).

Ya. I. Sakhno, S. V. Shishkina, O. V. Shishkin, M. I. Musatov, E. V. Vashchenko, S. M, Desenko, and V. A. Chebanov, Mol. Diversity, 14, 523 (2010).

Ya. I. Sakhno, S. M. Desenko, S. V. Shishkina, O. V. Shishkin, V. I. Musatov, and V. A. Chebanov, Synthesis, 1120 (2011).

V. A. Chebanov, Ya. I. Sakhno, and S. M. Desenko, Ultrason. Sonochem., 19, 707 (2012).

N. Yu. Gorobets, Yu. V. Sedash, K. S. Ostras, O. V. Zaremba, S. V. Shishkina, V. N. Baumer, O. V. Shishkin, S. M. Kovalenko, S. M. Desenko, and E. V. van der Eycken, Tetrahedron Lett., 51, 2095 (2010).

J. Světlik and V. Kettmann, Tetrahedron Lett., 52, 1062 (2011).

V. A. Chebanov, V. E. Saraev, S. M. Desenko, V. N. Chernenko, S. V. Shishkina, O. V. Shishkin, K. M. Kobzar, and C. O. Kappe, Org. Lett., 9, 1691 (2007).

A. Yu. Andriushchenko, S. M. Desenko, V. N. Chernenko, and V. A. Chebanov, J. Heterocycl. Chem., 48, 365 (2011).

V. Chebanov and S. Desenko, Multicomponent heterocyclizations with controlled selectivity. Reactions of carbonyl compounds with nitrogen-containing mono- bi-, and polynucleophiles. LAP LAMBERT Academic Publishing, Saarbrücken (2011).

E. A. Muravyova, S. V. Shishkina, V. I. Musatov, I. V. Knyazeva, O. V. Shishkin, S. M. Desenko, and V. A. Chebanov, Synthesis, 1375 (2009).

H.-G. Cheng, C.-B. Chen, F. Tan, N.-J. Chang, J.-R. Chen, and W.-J. Xiao, Eur. J. Org. Chem., 4976 (2010).

J. Sun, L.-L. Zhang, E.-Y. Xia, and C.-G. Yan, J. Org. Chem., 74, 3398 (2009).

S.-J. Tu, X.-D. Cao, W.-J. Hao, X.-H. Zhang, S. Yan, S,-S. Wu, Z.-G. Han, and F. Shi, Org. Biomol. Chem., 7, 557 (2009).

E. S. Gladkov, V. A. Chebanov, S. M. Desenko, O. V. Shishkin, S. V. Shishkina, D. Dallinger, and C. O. Kappe, Heterocycles, 73, 469 (2007).

R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, and T. A. Keating, Acc. Chem. Res., 29, 123 (1996).

S. M. Desenko, V. D. Orlov, and X. Estrada, Khim. Geterotsikl. Soedin., 999 (1990). [Chem. Heterocycl. Compd., 26, 839 (1990)].

V. M. Chernyshev, D. A. Khoroshkin, A. N. Sokolov, V. A. Taranushich, E. S. Gladkov, S. V. Shishkina, O. V. Shishkin, and S. M. Desenko, J. Heterocycl. Chem., 45, 1419 (2008).