Abstract
Base-induced cyclocondensation of acetoacetanilide (1) and benzoyl isothiocyanate (2) afforded mercaptopyridine (4). Compound 4 reacted with NaOCl in presence of NH4OH/NaOH to produce isothiazolopyridine (6). Heterocyclization of 4 by ethyl bromoacetate and/or phenacyl bromide afforded pyridothiazapene and pyridine derivatives 7, 8, respectively. The synthesis of pyrazolopyridine (9) was achieved by reaction of 4 with hydrazine hydrate. Oxidative cyclization of 4 by Br2 produced isothiazolopyridine (10). Chlorination of compound 4 yielded isothiazolopyridine dioxide (11). Compound 1 transformed into pyrane derivatives 12 and 13 by reaction with benzylidenemalononitrile and benzylideneacetophenone, respectively. Heterocyclization of compound 1 by ethylcyanoacetate and diethyloxalate afforded pyridine and cyclopentane derivatives 14 and 15, respectively. Compound 1 heterocyclized to indenopyrane (16) or indenopyrrole (17) upon reacted with ninhydrin on cold and hot condition, respectively. Heterocyclization of compound 1 and benzilmonohydrazone afforded pyridazine derivative 18. Coupling of 1 with diazonium salt afforded hydrazone 19 which cyclized using CS2/KOH gave pyridazine derivative 20.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
M. Movassaghi, M.D. Hill, O.K. Ahmad, J. Am. Chem. Soc. 129, 10096 (2007)
S.J. Teague, J. Org. Chem. 73, 9765 (2008)
P.R. Andres, U.S. Schubert, Adv. Mater. 16, 1043 (2004)
E.C. Constable, Chem. Soc. Rev. 36, 246 (2007)
M.W. Cooke, G.S. Hanan, Chem. Soc. Rev. 36, 1466 (2007)
D.G. Kurth, M. Higuchi, Soft Matter 2, 915 (2006)
E.A. Medlycott, G.S. Hanan, Chem. Soc. Rev. 34, 133 (2005)
Y. Zhou, T. Kijima, S. Kuwahara, M. Watanabe, T. Izumi, Tetrahedron Lett. 49, 3757 (2008)
J. Elguero, A.R. Katritzky, C.W. Ress, E.F. Scriven, in Comprehensive Heterocyclic Chemistry II, vol 3, eds. (Pergamon Press, Oxford, UK, 1996) p. 70
F.E. Goda, A.A.M. Abdel-Aziz, O.A. Attef, Bioorg. Med. Chem. 12, 1845 (2004)
V. Klimesová, M. Svoboda, K. Waisser, M. Pour, J. Kaustova, Il Farmaco. 54, 666 (1999)
T. Çolak, F. Çolak, O.Z. Yeşilel, E. Şahin, J. Iran. Chem. Soc. 7, 384 (2010)
M. Pregnolato, M. Terreni, D. Ubiali, G. Pagani, P. Borgna, F. Pastoni, F. Zapollo, Il Farmaco. 55, 669 (2000)
G. Bringmann, Y. Reichert, V. V Kane, Tetrahedron. 60, 3539 (2004)
S. Bondock, R. Rabie, H.A. Etman, A.A. Fadda, Eur. J. Med. Chem. 43, 2122 (2008)
R.M. Mohareb, J.Z. Ho, F.O. Alfarouk, J. Chin. Chem. Soc. 54, 4 (2007)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Sherif, M., Assy, M., Yousif, N. et al. Studies on heterocyclization of acetoacetanilide. J IRAN CHEM SOC 10, 85–91 (2013). https://doi.org/10.1007/s13738-012-0128-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13738-012-0128-x