A neat and rapid synthesis of 2-aryloxymethylene-6-arylimidazo [2,1-b]-1,3,4-thiadiazole under microwave irradiation

Synthetic Communications

Volumn 35, Issue 22, 2005, Pages 2881-2888

  Wang, Xicun ^a   Wang, Mangang ^a   Quan, Zhengjun ^a   Li, Zheng ^a  

^a NORTHWEST NORMAL UNIVERSITY   (China)

Author keywords

Imidazo 2,1 b 1,3,4 thiadiazole; Microwave irradiation; Synthesis

Indexed keywords

2 AMINO 5 ARYLOXYMETHYLENE 1,3,4 THIADIAZOLE; 2 ARYLOXYMETHYLENE 6 ARYLIMIDAZO[2,1 B] 1,3,4 THIADIAZOLE; ACETOPHENONE DERIVATIVE; PHENACYL BROMIDE; REAGENT; THIADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CRYSTAL; MICROWAVE IRRADIATION; POLYMERIZATION; PURIFICATION; SYNTHESIS;

EID: 29144444640     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500297289     Document Type: Article

References (20)

1. Terzioglu, N.; Gursoy, A. Synthesis and anticancer evaluation of some new hydrazone derivatives of 2,6-dimethylimidazo[2,1-b]-[1,3,4]thiadiazole-5- carbohydrazide. Eur. J. Med. Chem. 2003, 38, 781-786.
2. Gadad, A. K.; Noolvi, M. N.; Karpoormach, R. V. Synthesis and antitubercular activity of a series of 2-sulfonamido/trifluoromethyl-6-imidazo- [2,1-b]-1,3,4-thiadiazole derivatives. Bioorg. Med. Chem. 2004, 12, 5651-5659.
3. (a) Gadad, A. K.; Mahajanshetti, C. S.; Nimbalkar, S.; Raichurkar, A. Synthesis and antibacterial activity of some 5-guanylhydrazone/thiocyanato-6- arylimidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamide derivatives. Eur. J. Med. Chem. 2000, 35, 853-857;
4. (b) Mohan, J.; Varman, R. S. Bridgehead nitrogen heterocyclic systems: Facile synthesis and antimicrobial activity of imidazo[2,1-b]-1,3,4-thiadiazoles and thiadiazole[2′,3′:2,1]imidazo[4,5-b]quinoxaline. Ind. J. Heterocycl. Chem. 1999, 9 (2), 143-148.
5. Andotra, C. S.; Langer, T. C.; Kotha, A. Synthesis and antifungal activity of some substituted 1,3,4-thiadiazolo [3,2-a]-S-triazin-5-phenyl-7- thiones and imidazo-[2,1-b]-1,3,4-thiadiazole-5-ones. J. Indian Chem. Soc. 1997, 74 (2), 125-127.
6. Khazi, I. A. M.; Mahajanshetti, C. S.; Gadad, A. K.; Tarnalli, A. D.; Sultanpur, C. M. Synthesis and anticonvulsant and analgesic activities of some 6-substituted imidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamides and their 5-bromo derivatives. Arzneim-Forsch./Drug. Res. 1996, 46, 949-952.
7. Andreani, A.; Leonia, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Simon, W. A.; Senn-Bilfinger, J. Synthesis and antisecretory activity of 6-substituted-5-cyanomethylimidazo[2,1-b]thiazoles and 2,6-dimethyl-5- hydroxymethylimidazo[2,1-b][1,3,4]-thiadiazole. Arzneim./Drug. Res. 2000, 50, 550-553.
8. Andreani, A.; Bonazzi, D.; Rambaldi, M.; Fabbri, G.; Rainsford, K. D. Potential antitumor agents, VII allyl propargyl and cyanomethyl esters of imidazo[2, 1-b]thiazole-5-carboxylic acids. Eur. J. Med. Chem. 1982, 17, 271-274.
9. Andreani, A.; Rambaldi, M.; Mascellani, G.; Bossa, R.; Galatulas, I. Cardiotonic activity of 2,5-dimethoxyphenylimidazo[2,1-b]thiazoles. Eur. J. Med. Chem. 1986, 21, 451-453.
10. Andreani, A.; Rambaldi, M.; Mascellani, G.; Rugarli, P. Imidazothiazolecarboxaldehyde acetylhydrazones. Eur. J. Med. Chem. 1987, 22, 19-22.
11. Andreani, A.; Rambaldi, M.; Locatelli, A.; Andreani, F. 5-Formylimidazo[2,1-b]thiazoles and derivatives with herbicidal activity. Coll. Czech. Chem. Comm. 1991, 56, 2436-2447.
12. (a) Amery, W. K.; Hoerig, C. H.; Fenichel, R. I.; Chirigos, M. A. Eds.; Immune Modulation Agents and Their Mechanism; Marcel Dekker: New York, 1984; 383-408;
13. (b) Renoux, G.; Renoux, M. Immunostimulant effect of phenylimidothiazole derivatives on antibody-forming spleen cells. J. Immunol. 1972, 274, 756.
14. (a) Loupy, A.; Pigeon, P.; Ramdani, M. Synthesis of long chain aromatic esters in a solvent-free procedure under microwaves. Tetrahedron. 1996, 52 (19), 6705-6712;
15. (b) Marquez, H.; Perez, E. R.; Plutn, A. M.; Morales, M.; Loupy, A. Synthesis of 1-benzoyl-3-alkylthioureas by transamidation under microwave in dry media. Tetrahedron Lett. 2000, 41, 1753-1756.
16. (a) Wang, X. C.; Li, Z.; Zhang, Z. H.; Da, Y. X. Synthesis of 2-(4-chlorobenzoylamido)-5-aryloxymethyl-1,3,4-oxadiazoles under microwave irradiation. Synth. Commun. 2001, 31 (12), 1907-1911;
17. (b) Li, Z.; Wang, X. C.; Da, Y. X. Synthesis of 2-[5-(2-chlorophenyl)-2- furoylamido]-5-aryloxymethyl-1,3,4-thiadiazole under microwave irradiation. Synth. Commun. 2001, 31 (12), 1829-1836;
18. (c) Li, Z.; Wang, X. C. Synthesis of 1-aryloxyacetyl-4-(4-nitrobenzoyl)- thiosemicarbazides under phase-transfer catalysis and microwave irradiation. Synth. Commun. 2002, 32 (20), 3087-3092;
19. (d) Wang, X. C.; Li, Z.; Quan, Z. J.; Lu, X. S.; Gou, R. H. Solvent-free synthesis of 2-furyl-5-aryloxyacetylamido-1,3,4-thiadiazole under microwave irradiation. Synth. Commun. 2003, 33 (16), 2891-2897.
20. Wasfy, A. A .F.; Nassar, S. A.; Eissa, A. M. F. Heterocycles derived from 2-amine-5-[6-(dibenzothien-4-yl)-4,5-dihydropyridazin-3-yloxymethyl]-1,3,4- thiadiazole. Indian J. Chem., Sect. B 1996, 35, 1218-1220.