Methods have been developed for the preparation of 3-cyano-, 3-tetrazolyl-, and 3-acylamino derivatives of benzoselenophene, as well as a convenient method for the chlorination of benzoselenophene at the selenium atom using sulfuryl chloride to yield 1,1-dichloroselenophenes. The molecular structures of N-(benzoselenophen-3-yl)benzamide and N-(benzoselenophen-3-yl)-3-phenyl-acrylamide have been confirmed by X-ray structural analysis.
Similar content being viewed by others
References
J. A. Dodge, C. W. Lugar, S. Cho, J. J. Osborne, D. L. Phillips, A. L. Glasebrook, and C. A. Frolik, Bioorg. Med. Chem. Lett., 7, 993 (1997).
D. A. Bradley, A. G. Godfrey, and C. R. Schmid, Tetrahedron Lett., 40, 5155 (1999).
T. A. Grese, S. Cho, D. R. Finley, A. G. Godfrey, C. D. Jones, C. W. Lugar, III, M. J. Martin, K. Matsumoto, L. D. Pennington, M. A. Winter, M. Dee Adrian, H. W. Cole, D. E. Magee, D. Lynn Phillips, E. R. Rowley, L. L. Short, A. L. Glasebrook, and H. U. Bryant, J. Med. Chem., 40, 146 (1997).
M. J. Martin, T. A. Grese, A. L. Glasebrook, K. Matsumoto, L. D. Pennington, D. Lynn Phillips, and L. L. Short, Bioorg. Med. Chem. Lett., 7, 887 (1997).
A. D. Palkowitz, A. L. Glasebrook, K. Jeff Thrasher, K. L. Hauser, L. L. Short, D. Lynn Phillips, B. S. Muehl, M. Sato, P. K. Shetler, G. J. Cullinan, T. R. Pell, and H. U. Bryant, J. Med. Chem., 40, 1407 (1997).
C. R. Schmid, J. P. Sluka, and K. M. Duke, Tetrahedron Lett., 40, 675 (1999).
P. Arsenyan, I. Shestakova, K. Rubina, I. Domracheva, A. Nesterova, K. Vosele, O. Pudova, and E. Lukevics, Eur. J. Pharmacol., 465, 229 (2003).
P. Arsenyan, K. Rubina, I. Shestakova, E. Abele, R. Abele, I. Domracheva, A. Nesterova, J. Popelis, and E. Lukevics, Appl. Organomet. Chem., 17, 825 (2003).
P. Arsenyan, K. Rubina, I. Shestakova, and I. Domracheva, Eur. J. Med. Chem., 42, 635 (2007).
P. Arsenyan, E. Paegle, S. Belyakov, I. Shestakova, E. Jaschenko, I. Domracheva, and J. Popelis, Eur. J. Med. Chem., 46, 3434 (2011).
O. Behaghel and K. Hofmann, Chem. Ber., 72, 697 (1939).
T. M. Klapötke, B. Krumm, and M. Scherr, Z. Anorg. Allg. Chem., 636, 1955 (2010).
A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, and M. Camalli, J. Appl. Crystallogr., 27, 435 (1994).
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found Crystallogr., A64, 112 (2008).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 846–851, May, 2013.
Rights and permissions
About this article
Cite this article
Arsenyan, P., Paegle, E. & Belyakov, S. Synthesis of substituted benzo[b]selenophenes. Chem Heterocycl Comp 49, 791–796 (2013). https://doi.org/10.1007/s10593-013-1310-5
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-013-1310-5