Synthesis of some new thiazoles and pyrazolo[1,5-a]pyrimidines containing an antipyrine moiety

Synthetic Communications

Volumn 40, Issue 10, 2010, Pages 1539-1550

  Abdelhamid, Abdou O ^a   Afifi, Mamdouh A M ^a  

^a CAIRO UNIVERSITY   (Egypt)

Author keywords

Antipyrine; Coumarine; Pyrazoles; Pyrazolo 1,5 a pyrimidines; Thiazoles

Indexed keywords

2 (5 ACETYL 4 METHYL 3 PHENYL(1,3 THIAZOLIN 2 YLIDENE)) 2 [4 (2,3 DIMETHYL 5 OXO 1 PHENYL(3 PYRAZOLIN 4 YL))(1,3 THIAZOL 2 YL)]ETHANENITRILE; 2 (5 ACETYL 4 METHYL 3 PHENYL(1,3 THIAZOLIN 2 YLIDENE)) 2 [4 (2,3 DIMETHYL OXO 1 PHENYL(3 PYRAZOLIN 4 YL))(1,3 THIAZOL 2 YL)]ETHANENITRILE; 2 [4 (2,3 DIMETHYL 5 OXO 1 PHENYL (3 PYRAZOLIN 4 YL))(1,3 THIAZOL 2 YL)] 2 (4 OXO 3 PHENYL (1,3 THIAZOILIDIN 2 YLIDENE))ETHANENITRILE; 2 [4 (2,3 DIMETHYL 5 OXO 1 PHENYL(3 PYRAZOLIN 4 YL))(1,3 THIAZOL 2 YL)] 2 (3,4 DIPHENYL(1,3 THIADIAZOLIN 2 YLIDENE)ETHANENITRILE; 2 [4 (2,3 DIMETHYL 5 OXO 1 PHENYL(3 PYRAZOLIN 4 YL))(1,3 THIAZOL 2 YL)] 2 (4 METHYL 3 PHENYL(1,3 THIAZOLIN 2 YLIDENE))ETHANENITRILE; 2 [4 (2,3 DIMETHYL 5 OXO 1 PHENYL(3 PYRAZOLIN 4 YL))(1,3 THIAZOL 2 YL)] 3 METHYLTHIO 3 (PHENYLAMINO)PROP 2 ENENITRILE; 3 [4 (2,3 DIMETHYL 5 OXO 1 PHENYL 3 PYRAZOLIN 4 YL) 1,3 THIAZOL 2 YL] 2 CHROMEN 2 ONE; 3 [4 (2,3 DIMETHYL 5 OXO 1 PHENYL(3 PYRAZOLIN 4 YL))(1,3 THIAZOL 2 YL)] 7 METHYL 2 (PHENYLAMINO) 4,6,7,7A TETRAHYDROPYRAZOLO[1,5 A]PYRIMIDIN 5 ONE; 3 [4 (2,3 DIMETHYL 5 OXO 1 PHENYL(3 PYRAZOLIN 4 YL))(1,3 THIAZOL 2 YL)] 7 PHENYL 2 (PHENYLAMINO) 4,6,7,7A TETRAHYDROPYRAZOLO[1,5 A]PYRIMIDIN 5 ONE; 4 [2 (2 IMINO 2H CHROMEN 3 YL)THIAZOL 4 YL] 1,5 DIMETHYL 2 PHENYL 1,2 DIHYDROPYRAZOL 3 ONE; 4 [2 [4 AMINO 1 (4 METHYLPHENYL) 5 PHENYLCARBONYL)PYRAZOL 3 YL](1,3 THIAZOL 4 YL)] 2,3 DIMETHYL 1 PHENYL 3 PYRAZOLIN 5 ONE; 4 [2 [5 (1 AZA 2 (4 METHOXYPHENYLVINYL) 3 (PHENYLAMINO)PYRAZOL 4 YL](1,3 THIAZOL 2 YL)] 2,3 DIMETHYL 1 PHENYL 3 PYRAZOLIN 5 ONE; 4 [2 [5 (1 AZA 2 PHENYLVINYL) 3 (PHENYLAMINO)PYRAZOL 4 YL](1,3 THIAZOL 2 YL)] 2,3 DIMETHYL 1 PHENYL 3 PYRAZOLIN 5 ONE; 4 [2 [5 (1AZA 2 (4 CHLOROPHENYLVINYL) 3 (PHENYLAMINO)PYRAZOL 4 YL](1,3 THIAZOL 2 YL)] 2,3 DIMETHYL 1 PHENYL 3 PYRAZOLIN 5 ONE; 4 [2 [5 AMINO 3 (PHENYLAMINO)PYRAZOLIN 4 YL](1,3 THIAZOL 2 YL)] 2,3 DIMETHYL 1 PHENYL 3 PYRAZOLIN 5 ONE; 4 [2[5 (1 AZA 2 (4 METHYLPHENYLVINYL) 3 (PHENYLAMINO)PYRAZOL 4 YL](1,3 THIAZOL 2 YL)] 2,3 DIMETHYL 1 PHENYL 3 PYRAZOLIN 5 ONE; 4[ 2 [5,7 DIMETHYL 2 (PHENYLAMINO)(7A HYDROPYRAZOLO[1,5 A]PYRIMIDIN 3 YL](1, THIAZOL 4 YL)] 2,3 DIMETHYL 1 PHENYL 3 PYRAZOLIN 5 ONE; 7 AMINO 3 [4 (2,3 DIMETHYL 5 OXO 1 PHENYL(3 PYRAZOLIN 4 YL))(1,3 THIAZOL 2YL)] 5 PHENYL 2(PHENYLAMINO) 7A HYDROPYRAZOLO[1,5 A]PYRIMIDINE 6 CARBONITRILE; [4 (1,5 DIMETHYL 3 OXO 2 PHENYL 2,3 DIHYDRO 1H PYRAZOL 4 YL)THIAZOL 2 YL] (N' TOLYLHYDRAZINO)ACETONITRILE; [4 (1,5 DIMETHYL 3 OXO 2 PHENYL 2,3 DIHYDRO 1H PYRAZOL 4 YL)THIAZOL 2 YL] 3 PHENYLACRYLONITRILE; ACRYLONITRILE; ESTER; ETHYL 2 (CYANO (4 (2,3 DIHYDRO 1,5 DIMETHYL 3 OXO 2 PHENYL 1H PYRAZOL 4 YL)THIAZOL 2 YL)METHYLENE) 2, 3 DIHYDRO 4 METHYL 3 PHENYLTHIAZOLE 5 CARBOXYLATE; ETHYL 2 [2 [4 (2,3 DIMETHYL 5 OXO 1 PHENYL 3 (PYRAZOLIN 4 YL)] 2 CYANO 1 (PHENYL AMINO)VINYLTHIO]ACETATE; ETHYL 2[2 [4 (2,3 DIMETHYL 5 OXO 1 PHENYL 3 (PYRAZOLIN 4 YL)] 2 CYANO 1 (PHENYLAMINO)VINYLTHIO]ACETATE; ETHYL 2[[4 (2,3 DIMETHYL 5 OXO 1 PHENYL(3 PYRAZOLIN 4 YL))(1,3 THIAZOL 2 YL)]CYANO METHYLENE] 4 METHYL 3 PHENYL 1,3 THIAZOLINE 5 CARBOXYLATE; KETONE; PHENAZONE; PYRAZOLO[1,5 A]PYRIMIDINE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77951613004     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903100726     Document Type: Article

References (19)

1. Filho, V. C.; Correa, R.; Vaz, Z.; Calixto, J. B.; Nunes, R. J.; Pinheiro, T. R.; Andrico-pulo, A. D.; Yunes, R. A. Further studied on analgesic activity of cyclic imides. Farmaco 1998, 53, 55-57.
2. Sondhi, S. M.; Sharma, V. K.; Verma, R. P.; Singhal, N.; Shukla, R.; Raghubir, R.; Dubey, M. K. P. Synthesis, anti-inflammatory, and analgesic activity evaluation of some mercapto pyrimidine and pyrimidobenzimidazole derivatives. Synthesis 1999, 878-884 (Pubitemid 29227785)
3. Ismail, M. M. F.; Ammar, Y. A.; El-Zahaby, H. S. A.; Eisa, S. I.; El-Sayed Barakat, S. E. Synthesis of novel 1-pyrazolylpyridin-2-ones as potential anti-inflammatory and analgesic agent. Arch. Pharm. 2007, 340, 476-482
4. Mishra, A. P. J. Physicochemical and antimicrobial studies on nickel (II) and copper (II) Schiff base complexes derived from 2-furaldehyde. Ind. Chem. Soc. 1999, 76, 35-39.
5. Raman, N.; Kulandaisamy, A.; Jeyasubramanian, K. Synthesis, spectra, redox, and antimicrobial activity of Schiff base transition metal (II) complexes derived from 4-aminoantipyrine and benzyl. Synth. React. Inorg. Met. Chem. 2002, 32, 1583-1610.
6. Raman, N.; Kulandaisamy, A.; Jeyasubramanian, K. Synthesis, structural characterization, redox, and antibacterial studies of 12-membered tetraza macrocyclic Cu(II), Co(II), Zn(II), and VO(IV) complexes derived from 1,2-bis(imino-4-antipyrinyl)-1,2-dipheny-lethane o-phenylenediamine. Synth. React. Inorg. Met. Chem. 2004, 34, 17-43.
7. Sondhi, S. M.; Singhal, N.; Verma, R. P.; Arora, S. K.; Dastidar, S. G. Synthesis of heimn and porphyrin derivatives and their evaluation for anticancer activity. Ind. J. Chem. B 2001, 40, 113-119.
8. Lowe, P. A. Aromatic and heteroaromatic chemistry; In Heterocyclic Chemistry; H. Suschitzky, O. Meth-Cohn (Eds.); Chemical Society: London, 1980; vol.1, pp. 119-139.
9. Metzger, J. V. Thiazols and their benzo derivatives. In Comprehensive Heterocyclic Chemistry; A. R. Katritzky, C. W. Rees (Eds.); Pergamon Press: Oxford, UK, 1984; vol.6, p. 328.
10. Brown, H. D. 2-Pyronyl and 2-thiopyronyl benzazoles. US Patent 3,278,547, 1966; Chem. Abstr. 1966, 65, 18593.
11. Singh, S. P.; Segal, S. Synthesis and phototoxicity of some 2-(phenyl or 2-or 3-thienyl)-4-substituted thiazoles. Ind. J. Chem. B 1988, 27, 941.
12. Usui, Y.; Yamano, T. Fungicides, X. X: Antifungal activity of 3-aminothiazoline-2-thione and 4H-1,3,4-thidiazine derivatives. Yakugaku Zasshi 1969, 89, 099; Chem. Abstr. 1969, 71, 69601.
13. Goursot, P.; Westrum, E. F. Jr. Heat capacity and thermodynamic properties of ben-zothiazol from 5 to 320K. J. Chem. Eng. Data 1969, 14, 1.
14. Abdelhamid, A. O.; Emam, H. A.; Abdel-Reheem, N. A. Synthesis of some new 2,3-dihydro-1,3,4-thiadiazoles and arylazothiazoles. J. Chem. Res. 1999, (Synop.) 532= (Minipr.) 375, 2323.
15. Abdelhamid, A. O.; El-Ghandour, A. H.; Ahmed, S. A.; Zaki, Y. H. Synthesis and reactivity of 2-chloro-2-(hydroximino)-1-4-methyl-2-phenyl) thiazol-5-yl-1-one. J. Heterocycl. Chem. 2006, 43, 249.
16. Abdelhamid, A. O.; Sayed, A. R.; Zaki, Y. H. Reaction of hydrazonoyl halides 52: Synthesis and antimicrobial activity of some new pyrazolines and 1,3,4-thiadiazolines. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 1447.
17. Abdelhamid, A. O.; Sayed, A. R. Reaction of hydrazonoyl halides 51: A facile synthesis of 5-arylazothiazoles and triazolino[4,3-a]pyrimidines as antimicrobial activity. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 1766.
18. Abdelhamid, A. O.; Ismail, Z. H.; El-Gendy, M. S.; Ghorab, M. M. Reactions of hydra-zonoyl halides 53: Synthesis and antimicrobial activity of triazolino[4,3-a]pyrimidines and 5-arylazothiazoles as antimicrobial activity. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 2409.
19. Abdelhamid, A. O.; Afifi, M. A. M. Reactions with hydrazonoyl halides 61: Synthesis of 2,3-dihydro-1,3,4-Thiadiazoles. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 2713.