Heterocyclisation of substituted ylidenethiocarbonohydrazides using dimethyl acetylenedicarboxylate

References

Ahmadi, A., Saidi, K., & Khabazzadeh, H. (2009). An efficient synthesis of substituted 2-iminothiazolidin-4-one and thiadiazoloquinazolinone derivatives. Molecular Diversity, 13, 353-356. DOI: 10.1007/s11030-009-9124-1.10.1007/s11030-009-9124-1Search in Google Scholar PubMed

Alizadeh, A., Noaparast, Z., Sabahano, H., & Zohreh, N. (2010). One-pot, pseudo-five-component synthesis of bis[2- (arylimino)-1,3-thiazolidin-4-ones]. Helvatica Chimica Acta, 93, 1401-1406. DOI: 10.1002/hlca.200900402.10.1002/hlca.200900402Search in Google Scholar

Aly, A. A., Brown, A. B., & Hassan, A. A. (2014). Heterocycles from the reaction of thione groups with acetylenic bonds. Advances in Heterocyclic Chemistry, 113, 245-304. DOI: 10.1016/b978-0-12-800170-7.00005-5.10.1016/B978-0-12-800170-7.00005-5Search in Google Scholar

Bacchi, A., Carcelli, M., Pelagatti, P., Pelizzi, G., Rodriguez- Arguelles, M. C., Rogolino, D., Solinas, C., & Zani, F. (2005). Antimicrobial and mutagenic properties of organotin(IV) complexes with isatin and N-alkylisatin bisthiocarbonohydrazones. Journal of Inorganic Biochemistry, 99, 397-408. DOI: 10.1016/j.jinorgbio.2004.10.008.10.1016/j.jinorgbio.2004.10.008Search in Google Scholar PubMed

Balazs, F., Kudar, V., Csampai, A., Nagy, T. Z., & Sohar, P. (2007). Synthesis, IR-, NMR-, DFT and X-ray study of ferrocenyl heterocycles from thiosemicarbazones. Part 21: Study on ferrocenes. Journal of Organometallic Chemistry, 692, 5621-5632. DOI: 10.1016/j.jorganchem.2007.09.017.10.1016/j.jorganchem.2007.09.017Search in Google Scholar

Balazs, F., Csampai, A., Nagy, T. Z., Czugler, M., & Sohar, P. (2009). Synthesis, ring transformations, IR-, NMR and DFT study of heterocycles with two ferrocenyl units. Journal of Organometallic Chemistry, 694, 3732-3741. DOI: 10.1016/j.jorganchem.2009.07.038.10.1016/j.jorganchem.2009.07.038Search in Google Scholar

Bekircan, O., & Bekats, H. (2006). Synthesis of new bis-1,2,4- triazole derivatives. Molecules, 11, 469-477. DOI: 10.3390/11060469.10.3390/11060469Search in Google Scholar PubMed PubMed Central

Böhm, S., Tomaščikova, J., Imrich, J., Danihel, I., Kristian, P., Koch, A., Kleinpeter, E., & Klika, K. D. (2009). Computational study to assign structure, tautomerism, E/Z and s-cis/s-trans isomerism, π-delocalization, partial aromaticity and the ring size of 1,3-thiazolidin-4-ones and 1,3-thiazin-4-ones formed from thiosemicarbazides. Journal of Molecular Structure: Theochem, 916, 105-118. DOI: 10.1016/j.theochem.2009.09.019.10.1016/j.theochem.2009.09.019Search in Google Scholar

Dabholkar, V. V., & Ravi, T. D. (2010). Efficient synthesis of some novel spiro heterocycles containing triazine nucleus and their microbiological activity. Indian Journal of Chemistry, 49, 593-597.10.1002/chin.201038180Search in Google Scholar

Darehkordi, A., Saidi, K., & Islami,M. R. (2007). Preparation of heterocyclic compounds by reaction of dimethyl and diethyl acetylenedicarboxylate (DMAD, DEAD) with thiosemicarbazone derivatives. Arkivoc, 2007, 180-188.10.3998/ark.5550190.0008.120Search in Google Scholar

Dimmock, J. R., Kumar, P., Allen, T. M., Kao, G. Y., Halleran, S., Balzarini, J., & de Clercq, E. (1997). Synthesis and cytotoxic evaluation of some carbohydrazones and thiocarbohydrazones of various unsaturated ketones and related Mannich bases. Die Pharmazie, 52, 182-186.10.1002/chin.199727084Search in Google Scholar

Dvorko, M., Y., Albanov, A. I., Chipanina, N. N., Sherstyannikova, L. V., Samoilov, V. G., Komarova, T. N., & Glotova, T. E. (2006). New functionalized pyrazolines from 1-aroyl-2-phenylacetylenes and thiocarbonohydrazides. Chemistry of Heterocyclic Compounds, 42, 1421-1426. DOI: 10.1007/s10593-006-0258-0.10.1007/s10593-006-0258-0Search in Google Scholar

Ferrari, M. B., Capacchi, S., Pelosi, G., Reffo, G., Tarasconi, P., Albertini, R., Pinelli, S., & Lunghi, P. (1999). Synthesis, structural characterization and biological activity of helicin thiosemicarbazone monohydrate and a copper(II) complex of salicylaldehyde thiosemicarbazone. Inorganica Chimica Acta, 286, 134-141. DOI: 10.1016/s0020-1693(98)00383-1.10.1016/S0020-1693(98)00383-1Search in Google Scholar

Glotova, T. E., Dvorko, M. Y., Samoilov, V. G., & Ushakov, I. A. (2008). New 1,3,4-thiadiazole derivatives from 1- benzylidenethiocarbonohydrazides and 3-bromo-1-phenylprop-2-yn-1-one. Russian Journal of Organic Chemistry, 44, 866-869. DOI: 10.1134/s1070428008060158.10.1134/S1070428008060158Search in Google Scholar

Grangarapu, K., Manda, S., Jallapally, A., Thota, S., Karki, S. S., Balzarini, J., De Clercq, E., & Tokuda, H. (2014). Synthesis of thiocarbohydrazide and carbohydrazide derivatives as possible biologically active agents. Medicinal Chemistry Research, 23, 1046-1056. DOI: 10.1007/s00044-013-0684-3.10.1007/s00044-013-0684-3Search in Google Scholar PubMed PubMed Central

Hassan, A. A., Ibrahim, Y. R., El-Sheref, E. M., Aly, A. A., Brase, S., & Brown, A. B. (2012a). Novel synthesis of pyrazolyloxothiazolidine derivatives. Journal of Heterocyclic Chemistry, 49, 1380-1385. DOI: 10.1002/jhet.1023.10.1002/jhet.1023Search in Google Scholar

Hassan, A. A., Ibrahim, Y. R., El-Sheref, E. M., & Brown, A. B. (2012b). Novel synthesis of oxothiazolidine derivatives. Journal of Heterocyclic Chemistry, 49, 1054-1058. DOI: 10.1002/jhet.935.10.1002/jhet.935Search in Google Scholar

Hassan, A. A., Ibrahim, Y. R., Aly, A. A., El-Sheref, E. M., & Yamato, T. (2013). Reactions of dimethyl ethynedicarboxylate with (substituted ethylidene)hydrazinecarbothioamides. Journal of Heterocyclic Chemistry, 50, 473-477. DOI: 10. 1002/jhet.712.10.1002/jhet.712Search in Google Scholar

Hassan, A. A., Aly, A. A., Bedair, T. I. M., Brown, A. B., & El-Emary, T. I. (2014a). A facile method for the synthesis of hydrazine-4-oxothiazolidine and imino-5-oxothiadiazine derivatives from 1,4-disubstituted thiosemicarbazides. Journal of Heterocyclic Chemistry, 51, 44-49. DOI: 10.1002/jhet. 1655.Search in Google Scholar

Hassan, A. A., Mohamed, N. K., Abd El-Haleem, L. E., Brase, S., & Nieger, M. (2014b). Synthesis of some new heteroylhydrazono-1,3-thiazolidin-4-ones. Journal of Heterocyclic Chemistry, in press. DOI: 10.1002/jhet.2240.10.1002/jhet.2240Search in Google Scholar

Heravi, M. M., Nami, N., Neum¨uller, B., Oskooie, H. A., & Hekmatshoar, R. (2006). Synthesis of some trisubstituted thiazolidin-4-ones. Journal of Chemical Research, 2006, 722-724. DOI: 10.3184/030823406779173442.10.3184/030823406779173442Search in Google Scholar

Heravi, M. M., & Alishiri, T. (2014). Dimethyl acetylenedicarboxylate as a building block in heterocyclic synthesis. Advances in Heterocyclic Chemistry, 113, 1-66. DOI: 10.1016/b978-0-12-800170-7.00001-8.10.1016/B978-0-12-800170-7.00001-8Search in Google Scholar

Imrich, J., Tomaščikova, J., Danihel, I., Kristian, P., B¨ohm, S., & Klika, K. D. (2010). Selective formation of 5- or 6- membered rings, 1,3-thiazolidin-4-one vs. 1,3-thiazin-4-one, from acridine thiosemicarbazides by the use of ethyne acid esters. Heterocycles, 80, 489-503. DOI: 10.3987/com-09-s(s)56.10.3987/COM-09-S(S)56Search in Google Scholar

Kabashima, S., Okawara, T., Yamasaki, T., & Furukawa, M. (1990). Synthesis of novel 1,3-thiazolidines and 1,3,4- thiadiazolines from thiocarbohydrazines. Heterocycles, 31, 1129-1139. DOI: 10.3987/com-90-5380.10.3987/COM-90-5380Search in Google Scholar

Li, Z., Feng, X., & Zhao, Y. L. (2008). Microwave induced efficient synthesis of (un)substituted benzaldehyde (5- aryl-1,3,4-thiadiazol-2-yl)hydrazones using silica-supported dichlorophosphate as a recoverable dehydrant. Journal of Heterocyclic Chemistry, 45, 1489-1492. DOI: 10.1002/jhet. 5570450540.Search in Google Scholar

Naik, A. D., Annigeri, S. M., Gangadharmath, U. B., Revankar, V. K., & Mahale, V. B. (2002). Thiocarbohydrazide as ”diamine” to construct macrocyclic and side-off compart-mental ligands. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 43, 291-297. DOI: 10.1023/a:1021289104845.10.1023/A:1021289104845Search in Google Scholar

Nakarishi, K., & Solomon, P. H. (1977). Infrared absorption spectroscopy. San Francisco, CA, USA: Holden-Day.Search in Google Scholar

Rajendran, G., & Jain, S. R. (1984). Structural assignment of monothiocarbonohydrazones by 1H NMR spectroscopy. Organic Magnetic Resonance, 22, 6-10. DOI: 10.1002/mrc.1270220103.10.1002/mrc.1270220103Search in Google Scholar

Rhee, S. H. (1972). Synthesis and evaluation of antimicrobialantitumor activites of methylthiosemicarbazones and thiocarbohydrazones. Journal of the Pharmaceutical Society of Korea, 16, 162-175.Search in Google Scholar

Sahoo, M. K. (2007). Dimethyl acetylene dicarboxylate. Synlett, 2007, 2142-2143. DOI: 10.1055/s-2007-984894.10.1055/s-2007-984894Search in Google Scholar

Schrader, B. (1989). Raman/Infrared atlas of organic compounds. Weinheim, Germany: Wiley.Search in Google Scholar

Sengupta, P., Ghosh, S., & Mak, T. C. W. (2001). A new route for the synthesis of bis(pyridine dicarboxylato) bis(triphenylphosphine) complexes of ruthenium(II) and X-ray structural characterisation of the biologically active trans-[Ru(PPh3)2(L1H)2] (L1H2 = pyridine 2,3-dicarboxylic acid). Polyhedron, 20, 975-980. DOI: 10.1016/s0277-5387(01) 00736-7.Search in Google Scholar

Sheldrick, G. M. (2008). A short history of SHELX. Acta Crystallographic Section A, 64, 112-122. DOI: 10.1107/s0108767307043930.10.1107/S0108767307043930Search in Google Scholar PubMed

Shi, Z. C., Zhao, Z. G., Liu, X. L., & Wu, L. L. (2011). Synthesis of new deoxycholic acid bis thiocarbazones under solvent-free conditions using microwave irradiation. Journal of Chemical Research, 35, 198-201. DOI: 10.3184/174751911x12995267948561.10.3184/174751911X12995267948561Search in Google Scholar

Socrates, G. (1980). Infrared characterization group frequencies. New York, NY, USA:Wiley.Search in Google Scholar

Tomaščikova, J., Imrich, J., Danihel, I., B¨ohm, S., Kristian, P., Pisarčikova, J., Sabol, M., & Klika, K. D. (2008a).Search in Google Scholar

Regioselectivity and tautomerism of novel five-membered ring nitrogen heterocycles formed via cyclocondensation of acylthiosemicarbazides. Molecules, 13, 501-518. DOI: 10.3390/molecules13030501.10.3390/molecules13030501Search in Google Scholar PubMed PubMed Central

Tomaščikova, J., Danihel, I., B¨ohm, S., Imrich, J., Kristian, P., Potačňak, I., Čejka, J., & Klika, K. D. (2008b). Molecular and solid-state structure of methyl [2-(acridin-9-ylimino)-3-(tert-butylamino)-4-oxothiazolidin-5-ylidene]acetate. Journal of Molecular Structure, 875, 419-426. DOI: 10.1016/j. molstruc.2007.05.030. Search in Google Scholar