Abstract
Barton-Zard reaction of nitrostilbenes with ethyl isocyanoacetate carried out in EtOH in the presence of K2CO3 allowed us to minimize the formation of side products and to obtain 3,4-diarylpyrrole-2-carboxylates in high yields.
This is a preview of subscription content, log in via an institution to check access.
References
D. V. Demchuk, A. V. Samet, N. B. Chernysheva, V. I. Ushkarov, G. A. Stashina, L. D. Konyushkin, M. M. Raihstat, S. I. Firgang, A. A. Philchenkov, M. P. Zavelevich, L. M. Kuiava, V. F. Chekhun, D. Y. Blokhin, A. S. Kiselyov, M. N. Semenova, V. V. Semenov, Bioorg. Med. Chem., 2014, 22, 738.
D. V. Tsyganov, L. D. Konyushkin, I. B. Karmanova, S. I. Firgang, Y. A. Strelenko, M. N. Semenova, A. S. Kiselyov, V. V. Semenov, J. Nat. Prod., 2013, 76, 1485.
N. B. Chernysheva, A. S. Maksimenko, F. A. Andreyanov, V. P. Kislyi, Y. A. Strelenko, V. N. Khrustalev, M. N. Semenova, V. V. Semenov, Eur. J. Med. Chem., 2018, 146, 511.
V. V. Semenov, M. N. Semenova, Russ. Chem. Rev., 2015, 84, 134.
M. N. Semenova, D. V. Demchuk, D. V. Tsyganov, N. B. Chernysheva, A. V. Samet, E. A. Silyanova, V. P. Kislyi, A. S. Maksimenko, A. E. Varakutin, L. D. Konyushkin, M. M. Raihstat, A. S. Kiselyov, V. V. Semenov, ACS Comb.Sci., 20, 700–721; DOI: 10.1021/acscombsci.8b00113.
A. V. Samet, E. A. Sil´yanova, V. I. Ushkarov, M. N. Semenova, V. V. Semenov, Russ. Chem. Bull., 2018, 67, 858.
D. H. R. Barton, S. Z. Zard, J. Chem. Soc., Chem. Commun., 1985, 1098.
D. H. R. Barton, J. Kervagoret, S. Z. Zard, Tetrahedron, 1990, 46, 7587.
N. Ono, Heterocycles, 2008, 75, 243.
H. Fan, J. Peng, M. T. Hamann, J.-F. Hu, Chem. Rev., 2008, 108, 264.
N. Ono, H. Miyagawa, T. Ueta, T. Ogawa, H. Tani, J. Chem. Soc. Perkin Trans. 1, 1998, 1595.
A. Bhattacharya, S. Cherukuri, R. E. Plata, N. Patel, V. Tamez, J. A. Grosso, M. Peddicord, V. A. Palaniswamy, Tetrahedron Lett., 2006, 47, 5481.
P. Bobál, D. A. Lightner, J. Heterocycl. Chem., 2001, 38, 527.aaaaaaaa
J. A. Pfefferkorn, D. M. Bowles, W. Kissel, D. C. Boyles, C. Choi, S. D. Larsen, Y. Song, K.-L. Sun, S. R. Miller, B. K. Trivedi, Tetrahedron, 2007, 63, 8124.
Q. F. Liu, Adv. Mater. Res., 2014, 884–885, 465.
H. Uno, M. Tanaka, T. Inoue, N. Ono, Synthesis, 1999, 471.
J. G. Greger, S. J. P. Yoon-Miller, N. R. Bechtold, S. A. Flewelling, J. P. MacDonald, C. R. Downey, E. A. Cohen, E. T. Pelkey, J. Org. Chem., 2011, 76, 8203.
U. Robben, I. Lindner, W. Gärtner, J. Am. Chem. Soc., 2008, 130, 11303.
M. Caldarelli, J. Habermann, S. V. Ley, J. Chem. Soc., Perkin Trans. 1, 1999, 107.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2316–2319, December, 2018.
Rights and permissions
About this article
Cite this article
Silyanova, E.A., Samet, A.V. & Semenov, V.V. Efficient synthesis of 3,4-diarylpyrrole-2-carboxylates, the key fragments of natural antimitotic agents. Russ Chem Bull 67, 2316–2319 (2018). https://doi.org/10.1007/s11172-018-2375-1
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-018-2375-1