Microwave-Assisted Synthesis of Fused 3-Thiocarbamoylquinolines by Reinhoudt Reaction and their Modification by Hantzsch Reaction / Platonova A.Yu., Poluikova A.A., Trofimova O.A., Glukhareva T.V., Morzherin Yu.Yu. // Chemistry of Heterocyclic Compounds. - 2015. - V. 50, l. 10. - P. 1449-1455.

ISSN:

00093122

Type:

Article

Abstract:

We have shown that the reaction of 2-dialkylaminobenzaldehydes with cyanothioacetamide leading to Knoevenagel condensation products and their cyclization according to tert-amino effect mechanism, may be significantly accelerated by using a microwave reactor. The synthesized tetrahydroquinolino-3-carbothioamides reacted with α-bromoacetophenone in microwave reactor to give 3-(1,3-thiazol-2-yl)tetrahydroquinolines. © 2014 Springer Science+Business Media.

Author keywords:

Hantzsch reaction; Knoevenagel condensation; microwave irradiation; quinolines; Reinhoudt reaction; tert-amino effect; thiazoles; thioamides

Index keywords:

нет данных

DOI:

10.1007/s10593-014-1609-x

Смотреть в Scopus:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-84940363846&doi=10.1007%2fs10593-014-1609-x&partnerID=40&md5=609b6df56a7bf79fb7dcdaad5c12190b

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Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-84940363846&doi=10.1007%2fs10593-014-1609-x&partnerID=40&md5=609b6df56a7bf79fb7dcdaad5c12190b
Affiliations	Ural Federal University, 19 Mira St., Yekaterinburg, Russian Federation
Author Keywords	Hantzsch reaction; Knoevenagel condensation; microwave irradiation; quinolines; Reinhoudt reaction; tert-amino effect; thiazoles; thioamides
References	Meth-Cohn, O., (1996) Advances in Heterocyclic Chemistry, 65, p. 1. , A. R. Katritzky (editor), Academic Press, New York; Mátyus, P., Éliás, O., Tapolcsányi, P., Polonka-Bálint, Á., Halász-Dajka, B., (2006) Synthesis, p. 2625; Chen, W., Wilde, R.G., Seidel, D., (2014) Org. Lett., 16, p. 730. , 1:CAS:528:DC%2BC3sXhvFegtr7F; Belskaya, N.P., Bakulev, V.A., Deryabina, T.G., Subbotina, J.O., Kodess, M.I., Dehaen, W., Toppet, S., Van Meervelt, L., (2009) Tetrahedron, 65, p. 7662. , 1:CAS:528:DC%2BD1MXps1Cnsbk%3D; Povalyakhina, M.A., Pozharskii, A.F., Dyablo, O.V., Ozeryanskii, V.A., Ryabtsova, O.V., (2010) Mendeleev Commun., 20, p. 36. , 1:CAS:528:DC%2BC3cXitFKjtbg%3D; Verboom, W., Reinhoudt, D.N., (1990) Recl. Trav. Chim. Pays-Bas, 109, p. 311. , 1:CAS:528:DyaK3cXkslyiurY%3D; Platonova, A.Yu., Glukhareva, T.V., Zimovets, O.A., Morzherin, Yu.Yu., (2013) Chem. Heterocycl. Compd., 49, p. 357; (2013) Khim. Geterotsikl. Soedin., p. 386; Platonova, A.Yu., Deeva, E.V., Zimovets, O.A., Shatunova, D.V., El'tsov, O.S., Slepukhin, P.A., Glukhareva, T.V., Morzherin, Yu.Yu., (2011) Russ. Chem. Bull., Int. Ed., 60, p. 961; (2011) Izv. Akad. Nauk, Ser. Khim., 60, p. 937; D'yachenko, E., Glukhareva, T., Dyudya, L., Eltsov, O., Morzherin, Y., (2005) Molecules, 10, p. 1101; D'yachenko, E.V., Glukhareva, T.V., Nikolaenko, E.F., Tkachev, A.V., Morzherin, Yu.Yu., (2004) Russ. Chem. Bull., Int. Ed., 53, p. 1240; (2004) Izv. Akad. Nauk, Ser. Khim., 53, p. 1191; Krasnov, K.A., Kartsev, V.G., (2011) Chem. Nat. Compd., 46, p. 915; (2011) Khim. Prirod. Soedin., 46, p. 779; Glukhareva, T.V., Klimova, E.P., Platonova, A.Yu., Morzherin, Yu.Yu., (2008) Chem. Heterocycl. Compd., 44, p. 759; (2008) Khim. Geterotsikl. Soedin., p. 942; Ruble, J.C., Hurd, A.R., Johnson, T.A., Sherry, D.A., Barbachyn, M.R., Toogood, P.L., Bundy, G.L., Kamilar, G.M., (2009) J. Am. Chem. Soc., 131, p. 3991. , 1:CAS:528:DC%2BD1MXivVeisL4%3D; Glukhareva, T.V., Kropotina, P.E., Kosterina, M.F., Nein, Yu.I., Deeva, E.V., Morzherin, Yu.Yu., (2007) Chem. Heterocycl. Compd., 43, p. 76; (2007) Khim. Geterotsikl. Soedin., p. 90; Sather, A.C., Berryman, O.B., Rebek, J., Jr., (2012) Org. Lett., 14, p. 1600. , 1:CAS:528:DC%2BC38XjtFGmsbk%3D; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., Puschmann, H., (2009) J. Appl. Cryst., 42, p. 339. , 1:CAS:528:DC%2BD1MXjsFSnsbg%3D
Correspondence Address	Morzherin, Yu.Yu.; Ural Federal University, 19 Mira St., Russian Federation
Publisher	Springer New York LLC
CODEN	CHCCA
Language of Original Document	English
Abbreviated Source Title	Chem. Heterocycl. Compd.
Source	Scopus