Alumina Catalyzed Synthesis of Fused Thioxopyrimidine Derivatives under Microwaves

Synthetic Communications

Volumn 33, Issue 21, 2003, Pages 3747-3759

  Kidwai, M ^a   Mohan, R ^a   Rastogi, S ^a  

^a UNIVERSITY OF DELHI   (India)

Author keywords

Alumina; Catalyst; Dry media; Microwave irradiation; Solid support; Thioxopyrimidines

Indexed keywords

ALUMINUM OXIDE; IMINOPYRIMIDINO[4,5 D]PYRIMIDIDNE; ISOXAZOLINO[3,4 D]PYRIMIDIDNE; PYRANO[2,3 D]PYRIMIDIDNE; PYRAZOLINO[3,4 D]PYRIMIDINE; PYRIMIDINE DERIVATIVE; THIAZINO[5,4 D]PYRIMIDINE; THIOBARBITURIC ACID; THIOXOPYRIMIDINO[4,5 D]PYRIMIDINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; MICROWAVE RADIATION; SOLID; SYNTHESIS; TIME;

EID: 0242331189     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120025184     Document Type: Article

References (34)

1. Yoo, M.-H.; Kim, W.-B.; Chang, M.-S.; Kim, S.-H.; Kim, D.-S.; Bae, C.-J. ; Kim, Y.-D.; Kim, E.-H. A process for preparing pyrazolopyrimidinone derivatives for the treatment of impotence, PCT Int. Appl. WO 01 98304. Chem. Abstr. 2002, 136, 53762.
2. Ankhiwala, M.D.; Hathi, M.V. Synthesis and antibacterial activity of some 1-phenyl-3,5-diaryl-1,2-pyrazolines and 3,5-diaryl 1,2-isoxazolines. J. Indian Chem. Soc. 1994, 71, 587-589.
3. Himmelsback, F.; Dahmann, G.; Von Ruden, T.; Metz, T. Preparation of pyrimido[5,4-d] pyrimidines as tyrosine kinase signal transduction inhibitors. PCT Int. Appl. WO 97 32880. Chem. Abstr. 1997, 127, 278206.
4. Smissmann, E.; Robinson, R.A.; Matuszak, A.J. Prevost reaction with 5-substituted-5-allyl barbituric acids. J. Org. Chem. 1970, 35, 3823-3824.
5. Ahluwalia, V.K.; Chopra, M.; Chandra, R. A convenient synthesis of novel pyrimidine analogs of o-hydroxy chalcones and pyrano [2,3-d] pyrimidines and their biological activities. J. Chem. Res. (S) 2000, 162-163.
6. Allerton, C.M.N.; Barber, C.G.; Maw, G.N.; Rawson, D.J. Preparation of pyrazolo[4,3-d]pyrimidin-7-ones as phosphodiesterase inhibitors. PCT Int. Appl. WO 01 27112. Chem. Abstr. 2001, 134, 311220.
7. Dunn, J.P.; Goldstein, D.M.; Harris, W.; Smith, I.E.D.; Welch, T.R. Preparation of alkylamino substituted bicyclic nitrogen heterocycles for pharmaceutical use as inhibitors of p38 protein kinase. PCT Int. Appl. WO 01 29041. Chem. Abstr. 2001, 134, 311223.
8. Sammour, A.E.A. Behaviour of o-hydroxy chalcones towards the action of phenylhydrazine, hydroxylamine, primary aliphatic amines and paraformaldehyde. Tetrahedron 1964, 20, 1067-1071.
9. Raval, A.A.; Thakor, V.M.; Shah, N.M. Synthesis of some 1,3,5-triphenyl pyrazolines and 3,5-diphenyl-cyclohexen-I-ones. J. Indian Chem. Soc. 1963, 40, 323-324.
10. Ahluwalia, V.K.; Kumar, R.; Alauddin, M.; Khanduri, C.H.; Mallika, N. A convenient one pot synthesis of 1,3,5-triaryl-1,2,3,4-tetrahydro-4-oxo-7-methyl-2-thioxo-5H-pyrano[2,3-d] pyrimidines. Synth. Commun. 1990, 20 (9), 1265-1272.
11. Sedova, V.F.; Samsonov, V.A.; Mamaev, V.P. Reaction of chalcones with arylidenebisureas, Izv. Sib. Otd. Akad. Nauk, SSSR, Ser. Khim. Nauk 1972, 2, 112-115; Chem. Abstr. 1972, 77, 164635
12. Sedova, V.F.; Samsonov, V.A.; Mamaev, V.P. Reaction of chalcones with arylidenebisureas, Izv. Sib. Otd. Akad. Nauk, SSSR, Ser. Khim. Nauk 1972, 2, 112-115; Chem. Abstr. 1972, 77, 164635.
13. Das, P.K.; Behera, G.B.; Sahay, A.K.; Mishra, B.K. Synthesis of pyrazolo[3,4-d]pyrimidines and isoxazolo[3,4-d]pyrimidines, Indian J. Chem. Sect. B; Org. Chem. Incl. Med. Chem 1985, 24B, 437-439.
14. Bunnage, M.E.; Levett, P.C.; Thomson, N.M. Novel process for the preparation of pyrazolopyrimidinones. PCT Int. Appl. WO 01 98 303. Chem. Abstr. 2002, 136, 53761.
15. Rudorf, W.D.; Koeditz, J.; Henze, N. Acylformylketene acetals: Versatile synthons for the synthesis of isoxazoles, pyrazoles and pyrimidines. Sulfur Lett. 1993, 16 (2), 77-89.
16. Varma, R.S. Solvent-free organic synthesis using supported reagents and microwave irradiation. Green Chemistry 1999, 1, 43-55.
17. (a) Kidwai, M.; Venkataramanan, R.; Garg, R.K.; Bhushan, K.R. Novel one pot synthesis of new pyranopyrimidines using microwaves. J. Chem. Res. (S), 2000, 586-587;
18. (b) Kidwai, M.; Sapra, P. An efficient synthesis of benzopyrano pyrimidines using inorganic solid support. Synth. Commun. 2002, 32 (11), 1639-1645.
19. Kidwai, M.; Misra, P. Ring closure reactions of chalcones using microwave technology. Synth. Commun. 1999, 29 (18), 3237-3250.
20. Kidwai, M.; Misra, P.; Bhushan, K.R. Alumina supported synthesis of thiadiazolyl thiazolothiones. Synth. Commun. 2001, 31 (6), 19-24.
21. Kidwai, M.; Sapra, P.; Bhushan, K.R.; Misra, P. Microwave assisted solid-support synthesis of pyrazolino/iminopyrimidino/thioxopyrimidino imidazoles. Synthesis 2001, 10, 1509-1512.
22. Kidwai, M. Dry media reactions. Pure Appl. Chem. 2001, 73 (1), 147-151.
23. (a) Solid Supports and Catalysis in Organic Synthesis; Smith, K., Ed.; Ellis Horwood, PTR Prentice Hall: Chichester, 1992;
24. (b) Clark, J.H. Catalysis of organic reactions by supported inorganic reagents; VCH: Weinheim, 1994.
25. (a) Vvedenskii, V.M.; Makukha, M.P.; Makarina-Kibak, Ya. Substitution in barbituric acid II. Condensation of thiobarbituric acid with oxo compounds. Chem. Heterocyclic Compds. 1969, 5, 1096-1098;
26. (b) Suvorov, N.N.; Velezheva, V.S.; Vampilova, V.V. Synthesis of 5-(3-indolylmethyl)barbituric and thiobarbituric acids, Khim. Geterotsikl. Soedin 1974, 5, 646-649.
27. Joshi, K.C.; Jauhar, A.K. Synthesis of some pyrazolines and iso-oxazolines. J. Indian Chem. Soc. 1965, 42, 733-734.
28. Davey, W.; Guilt, J.R. Chalcones and related compounds. Part II. Addition of thiols and esters to the chalcone system. J. Chem. Soc. 1957, 1015-1017.
29. EL-Rayyes, N.R. Heterocycles. Part I. A new route to the synthesis of substituted 2-aminopyrimidines. J. Heterocyclic Chem. 1982, 19, 415-419.
30. Van Allan, J.A.; Reynolds, G.A. The preparation of certain pyrylium salts by using chalcone and boron trifluoride etherate. J. Org. Chem. 1968, 33, 1102-1105.
31. Dhar, D.N.; Singh, A.K. Reaction of chalkone with thiourea: synthesis-of 2-oxo-1,3-thiazine system and substituted cyclobutanes. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1979, 17B, 25-27.
32. 2/g) was used;
33. 2/g) was used;
34. 2/g) was used.