Recyclization of carbonyl-substituted 4H-chromenes and 1H-benzo[f]chromenes by the action of amidines and guanidine: a novel method for the synthesis of ortho-hydroxybenzylpyrimidines

Author:

Popova Yulia V.,Sakhnenko Darina V.,Arbuzova Irina V.,Osyanin Vitaly A.,Osipov Dmitry V.,Klimochkin Yuri N.

Publisher

Springer Science and Business Media LLC

Subject

Organic Chemistry

Reference5 articles.

1. (a) Parmar, V. S.; Tyagi, O. D.; Malhotra, A.; Singh, S. K.; Bisht, K. S.; Jain, R. Nat. Prod. Rep. 1994, 11, 219. (b) Osyanin, V. A.; Borisov, D. D.; Osipov, D. V.; Klimochkin, Yu. N. Russ. J. Org. Chem. 2014, 50, 1590. [Zh. Org. Khim. 2014, 50, 1604.] (c) Forseth, R. R.; Fox, E. M.; Chung, D.; Howlett, B. J.; Keller, N. P.; Schroeder, F. C. J. Am. Chem. Soc. 2011, 133, 9678. (d) Hiltunen, L. H.; Laakso, I.; Chobot, V.; Hakala, K. S.; Weckman, A.; Valkonen, J. P. T. J. Agric. Food Chem. 2006, 54, 3372.

2. (a) Durrant, J. D.; Carlson, K. E.; Martin, T. A.; Offutt, T. L.; Mayne, C. G.; Katzenellenbogen, J. A.; Amaro, R. E. J. Chem. Inf. Model 2015, 55, 1953. (b) Rosowsky, A.; Forsch, R. A.; Sibley, C. H.; Inderlied, C. B.; Queener, S. F. J. Med. Chem. 2004, 47, 1475. (c) Rotili, D.; Carafa, V.; Tarantino, D.; Botta, G.; Nebbioso, A.; Altucci, L.; Mai, A. Bioorg. Med. Chem. 2011, 19, 3659. (d) Kelly, T. A.; Proudfoot, J. R.; McNeil, D. W.; Patel, U. R.; David, E.; Hargrave, K. D.; Grob, P. M.; Cardozo, M.; Agarwal, A.; Adams, J. J. Med. Chem. 1995, 38, 4839.

3. (a) Linsenmeier, A. M.; Bräse, S. Eur. J. Org. Chem. 2012, 6455. (b) Katritzky, A. R.; Belyakov, S. A.; Fang, Y.; Kiely, J. S. Tetrahedron Lett. 1998, 39, 8051. (c) Osyanin, V. A. Thesis Dr. Chemistry; Samara, 2014. [ http://d21221705.samgtu.ru/sites/d21221705.samgtu.ru/files/osyaninv.pdf ].

4. (a) Fandrick, D. R.; Reinhardt, D.; Desrosiers, J.-N.; Sanyal, S.; Fandrick, K. R.; Ma, S.; Grinberg, N.; Lee, H.; Song, J. J.; Senanayake, C. H. Org. Lett. 2014, 16, 2834. (b) Seleem, M. A.; Disouky, A. M.; Mohammad, H.; Abdelghany, T. M.; Mancy, A. S.; Bayoumi, S. A.; Elshaffey, A.; El-Morsy, A.; Seleem, M. N.; Mayhoub, A. S. J. Med. Chem. 2016, 59, 4900.

5. (a) Lukashenko, A. V.; Osyanin, V. A.; Osipov, D. V.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2016, 52, 711. [Khimiya geterotsikl. soedinenii 2016, 52, 711.] (b) Osyanin, V. A.; Lukashenko, A. V.; Osipov, D. V.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2015, 50, 1528. [Khim. Geterotsikl. Soedin. 2014, 1663.] (c) René, L. Synthesis 1989, 69.

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