An efficient one-pot synthesis of new 2-imino-1,3-thiazolidin-4-ones under ultrasonic conditions

Ultrasonics Sonochemistry

Volumn 18, Issue 1, 2011, Pages 45-48

  Mamaghani, Manouchehr ^a   Loghmanifar, Azam ^a   Taati, Mohammad Reza ^a  

^a UNIVERSITY OF GUILAN   (Iran)

Author keywords

Iminothiazolidinone; Multicomponent; One pot; Thiourea; Ultrasound

Indexed keywords

CHLORINE COMPOUNDS; THIOUREAS; ULTRASONICS;

HIGH YIELD; IMINOTHIAZOLIDINONE; MULTICOMPONENTS; ONE POT; ONE-POT PROTOCOL; ONE-POT SYNTHESIS;

SODIUM HYDROXIDE;

2 CYCLOHEXYLIMINO 3 ETHYLTHIAZOLIDIN 4 ONE; 2 IMINO 1,3 THIAZOLIDIN 4 ONE DERIVATIVE; 2 IMINO 5 4 TOLYLTHIAZOLIDIN 4 ONE; 2 IMINO 5 PHENYLTHIAZOLIDIN 4 ONE; 3 ALLYL 2 (4 TOLYLIMINO)THIAZOLIDIN 4 ONE; 3 ALLYL 2 (THIAZOL 2 YLIMINO)THIAZOLIDIN 4 ONE; 3 BENZYL 2 (PHENYLIMINO)THIAZOLIDIN 4 ONE; 3 BENZYL 5 PHENYL 2 (PHENYLIMINO)THIAZOLIDIN 4 ONE; 3 CYCLOHEXYL 2 (ETHYLIMINO)THIAZOLIDIN 4 ONE; 3 ETHYL 2 (4 TOLYLIMINO)THIAZOLIDIN 4 ONE; 3 ETHYL 5 PHENYL 2 (4 TOLYLIMINO)THIAZOLIDIN 4 ONE; 5 PHENYL 2 (4 TOLYLIMINO)THIAZOLIDIN 4 ONE; ALDEHYDE DERIVATIVE; AMINE; CHLOROFORM; ISOCYANATE; SODIUM HYDROXIDE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ONE POT SYNTHESIS; PRIORITY JOURNAL; REACTION TIME; ROOM TEMPERATURE; ULTRASOUND;

EID: 77956493740     PISSN: 13504177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ultsonch.2010.05.009     Document Type: Article

References (35)

1. Klika K.D., Janovec L., Imrich J., Suchar G., Kristian P., Sillanpaa R., Pihlaja K. Regioselective synthesis of 2-imino-1,3-thiazolidin-4-ones by treatment of N-(anthracen-9-yl)-N-ethylthiourea with bromoacetic acid derivatives. Eur. J. Org. Chem. 2002, 1248.
2. Kline T., Felise H.B., Barry K.C., Jackson S.R., Nguyen H.V., Miller S.I. Substituted 2-imino-5-arylidenethiazolidin-4-one inhibitors of bacterial type III secretion. J. Med. Chem. 2008, 51:7065.
3. Rahman V.P.M., Mukhtar S., Ansari W.H., Lemiere G. Synthesis, stereochemistry and biological activity of some novel long alkyl substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide. Eur. J. Med. Chem. 2005, 40:173.
4. Gursoy A., Terzioglu N. Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anti-convulsant activity. Turk J. Chem. 2005, 29:247.
5. Blanchet J., Zhu J. Reeve's synthesis of 2-imino-4-thiazolidinone from alkyl (aryl) trichloromethylcarbinol revisited, a three-component process from aldehyde, chloroform and thiourea. Tetrahedron Lett. 2004, 45:4449.
6. Ottana R., Maccari R., Barreca M.L., Bruno G., Rotondo A., Rossi A., Chiricosta G., Paola R., Sautebin L., Cuzzocread S., Vigorita M.G. 5-Arylidene-2-imino-4-thiazolidinones: design and synthesis of novel anti-inflammatory agents. Bioorg. Med. Chem. 2005, 13:4243.
7. Singh S.P., Parmar S.S., Raman K., Stenberg V.I. Chemistry and biological activity of thiazolidinones. Chem. Rev. 1981, 81:175.
8. Newkome G.R., Nayak A. 4-Thiazolidinones. Adv. Heterocycl. Chem. 1980, 25:83.
9. Kandeel K.A. Synthesis and structures of some new thiazolidin-4-ones and thiazolin-4-ones of anticipated biological activity. ARKIVOC 2006, 1.
10. Liu Z., Huang Y., Zhang W., Ma L., Li J., Wang X., Li J., Shen J. Soluble polymer-supported synthesis of 5-arylidene thiazolidinones and pyrimidinones using a novel traceless linker strategy. J. Comb. Chem. 2008, 10:632.
11. Laurent D.R., Gao Q., Wu D., Serrano-Wu M.H. Regioselective synthesis of 3-(heteroaryl)-iminothiazolidin-4-ones. Tetrahedron Lett. 2004, 45:1907.
12. Sedlak M., Hanusek J., Machacek V., Hejtmankova L. Synthesis and ring transformation of substituted S-(1-phenylpyrrolidine-2-ones-3-yl)isothiuronium salts to substituted 2-imino-5-[2-(phenylamino)ethyl]thiazolidin-4-ones. J. Heterocycl. Chem. 2002, 39:1105.
13. Reeve W., Nees M. Reactions of aryl(trichloromethyl)carbinols with sulfur nucleophiles. Formation and proof of zwitterionic structure of iminothiazolidinones. J. Am. Chem. Soc. 1967, 89:647.
14. Marechal A.M., Robert A., Leban I. Gem dicyano époxydes équivalents synthétiques des dications cétènes: synthése de thiazolidinone-4 par réaction avec des thiourées substituées et évolution particulière en (aryl-cyanoformyl) méthylène-2 benzoxazole par réaction avec le thioxo-2 benzoxazole. Tetrahedron 1990, 46:453.
15. Baudy M., Robert A., Foucaud A. Reaction of N-substituted thioamides with gem-dicyano epoxides: a new synthetic route to anhydro-4-hydroxythiazolium hydroxides. J. Org. Chem. 1978, 43:3732.
16. Matloubi Moghaddam F., Hojabri L. A novel synthesis of some 2-imino-4-thiazolidinone derivatives. J. Heterocycl. Chem. 2007, 44:35.
17. 2 in water. Ultrason. Sonochem. 2009, 16:7.
18. Cravotto G., Cintas P. Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications. Chem. Soc. Rev. 2006, 35:180.
19. T.J. Mason, J.P. Lorimer, Applied Sonochemistry, The Uses of Power Ultrasound in Chemistry and Processing, Wiley VCH, Verlag GmbH, 2002.
20. Mantu D., Moldoveanu C., Nicolescu A., Deleanu C., Mangalagiu I.I. A facile synthesis of pyridazinone derivatives under ultrasonic irradiation. Ultrason. Sonochem. 2009, 16:452.
21. Li J.-T., Yin Y., Li L., Sun M.-X. A convenient and efficient protocol for the synthesis of 5-aryl-1,3-diphenylpyrazole catalyzed by hydrochloric acid under ultrasound irradiation. Ultrason. Sonochem. 2010, 17:11.
22. Pizzuti L., Martins P.L.G., Ribeiro B.A., Quina F.H., Pinto E., Flores A.F.C., Venzke D., Pereira C.M.P. Efficient sonochemical synthesis of novel 3,5-diaryl-4,5-dihydro-1H-pyrazole-1-carboximidamides. Ultrason. Sonochem. 2010, 17:34.
23. Ni C.-L., Song X.-H., Yan H., Song X.-Q., Zhong R.-G. Improved synthesis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylate under ultrasound irradiation. Ultrason. Sonochem. 2010, 17:367.
24. Bazgir A., Ahadi S., Ghahremanzadeh R., Khavasi H.R., Mirzaei P. Ultrasound-assisted one-pot, three-component synthesis of spiro[indoline-3,4'-pyrazolo[3,4-b]pyridine]-2,6'(1'H)-diones in water. Ultrason. Sonochem. 2010, 17:447.
25. Zhang Z.-H., Li J.-J., Li T.-S. Ultrasound-assisted synthesis of pyrroles catalyzed by zirconium chloride under solvent-free conditions. Ultrason. Sonochem. 2008, 15:673.
26. 4 under ambient conditions. Ultrason. Sonochem. 2008, 15:659.
27. Nikpassand M., Mamaghani M., Shirini F., Tabatabaeian K. A convenient ultrasound-promoted regioselective synthesis of fused polycyclic 4-aryl-3-methyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridines. Ultrason. Sonochem. 2010, 17:301.
28. Mamaghani M., Dastmard S. An efficient ultrasound-promoted synthesis of the Baylis-Hillman adducts catalyzed by imidazole and l-proline. Ultrason. Sonochem. 2009, 16:445.
29. Tabatabaeian K., Mamaghani M., Mahmoodi N., Khorshidi A. Ultrasonic-assisted ruthenium-catalyzed oxidation of aromatic and heteroaromatic compounds. Catal. Commun. 2008, 9:416.
30. Nikpassand M., Mamaghani M., Tabatabaeian K. An efficient one-pot three-component synthesis of fused 1,4-dihydropyridines using HY-zeolite. Molecules 2009, 14:1468.
31. Mamaghani M., Dastmard S. One-pot easy conversion of Baylis-Hillman adducts into arylpyrazoles under ultrasound irradiation. ARKIVOC 2009, 168.
32. Samimi H.A., Mamaghani M., Tabatabaeian K. An efficient synthesis of 5-benzoyloxazolines by regio- and stereo-controlled reaction of N-substituted 2-benzoylaziridines under microwave irradiation. J. Heterocycl. Chem. 2008, 45:1765.
33. Tabatabaeian K., Mamaghani M., Mahmoodi N., Khorshidi A. Solvent-free, ruthenium-catalyzed, regioselective ring-opening of epoxides, an efficient route to various 3-alkylated indoles. Tetrahedron Lett. 2008, 49:1450.
34. Manson T.J. Ultrasound in synthetic organic chemistry. Chem. Soc. Rev. 1997, 26:443.
35. Samimi H.A., Mamaghani M., Tabatabaeian K. A convenient one-pot three component approach to synthesis of higly substituted iminothiazolines. Heterocycles 2008, 75:2825.