Reaction of phthalhydrazide and acetylenedicarboxylates in the presence of N-heterocycles: an efficient synthesis of phthalazine derivatives

Tetrahedron Letters

Volumn 49, Issue 29-30, 2008, Pages 4479-4482

  Ghahremanzadeh, Ramin ^a   Ahadi, Somayyeh ^a   Sayyafi, Maryam ^a   Bazgir, Ayoob ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Dialkyl acetylenedicarboxylates; Imidazole; Isoquinoline; Phthalhydrazide; Quinoline

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; DIETHYL 2 [1 [1,4 DIOXO 3,4 DIHYDROPHTHALAZIN 2 (1H)YL]ISOQUINOLIN 2 (1H)YL]FUMARATE; DIETHYL 2 [1,4 DIOXO 3,4 DIHYDROPHTHALAZIN 2 (1H)YL]FUMARATE; DIMETHYL 2 [1 [1,4 DIOXO 3,4 DIHYDROPHTHALAZIN 2 (1H)YL]ISOQUINOLIN 2 (1H)YL]FUMARATE; DIMETHYL 2 [1,4 DIOXO 3,4 DIHYDROPHTHALAZIN 2 (1H)YL]FUMARATE; DIMETHYL 2 [2 [1,4 DIOXO 3,4 DIHYDROPHTHALAZIN 2 (1H)YL] 3 METHYL 2,3 DIHYDRO 1H IMIDAZOL 1 YL]FUMARATE; ETHYL 2 [1 METHYL 6,8,13 TRIOXO 1,8,13,14ATETRAHYDROIMIDAZO[2',1':3,4][1,2,4]TRIAZINO[1,2 B] PHTHALAZIN 5 (6H)YLIDENE]ETHANOATE; HYDRAZIDE DERIVATIVE; PHTHALAZINE DERIVATIVE; PHTHALHYDRAZIDE; TERT BUTYL 2 [1 METHYL 6,8,13 TRIOXO 1,8,13,14ATETRAHYDROIMIDAZO[2',1':3,4][1,2,4]TRIAZINO[1,2 B] PHTHALAZIN 5 (6H)YLIDENE]ETHANOATE;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 44749084518     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.063     Document Type: Article

References (27)

1. Gribble G.W. In: Katrizky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 2 (1996), Elsevier, Oxford 207
2. Acheson R.M. Adv. Heterocycl. Chem. 1 (1963) 125
3. Acheson R.M., and Elmore N.F. Adv. Heterocycl. Chem. 23 (1978) 263
4. Alo-Assar F., Zelenin K.N., Lesiovskaya E.E., Bezhan I.P., and Chakchir B.A. Pharm. Chem. J. 36 (2002) 598
5. Jain R.P., and Vederas J.C. Bioorg. Med. Chem. Lett. 14 (2004) 3655
6. Carling R.W., Moore K.W., Street L.J., Wild D., Isted C., Leeson P.D., Thomas S., O'Conner D., McKernan R.M., Quirk K., Cook S.M., Atack J.R., Waftord K.A., Thompson S.A., Dawson G.R., Ferris P., and Castro J.L. J. Med. Chem. 47 (2004) 1807
7. Grasso S., DeSarro G., Micale N., Zappala M., Puia G., Baraldi M., and Demicheli C. J. Med. Chem. 43 (2000) 2851
8. Nomoto Y., Obase H., Takai H., Teranishi M., Nakamura J., and Kubo K. Chem. Pharm. Bull. 38 (1990) 2179
9. Watanabe N., Kabasawa Y., Takase Y., Matsukura M., Miyazaki K., Ishihara H., Kodama K., and Adachi H. J. Med. Chem. 41 (1998) 3367
10. Sheradsky T., and Moshenberg R. J. Org. Chem. 51 (1986) 3123
11. Heine H.W., Baclawski L.M., Bonser S.M., and Wachob G.D. J. Org. Chem. 41 (1976) 3229
12. Ramtohup Y.K., James M.N.G., and Vederas J.C. J. Org. Chem. 67 (2002) 3169
13. Liu L.P., Lu J.M., and Shi M. Org. Lett. 9 (2007) 1303
14. Csampai A., Kormendy K., and Ruff F. Tetrahedron 47 (1991) 4457
15. Amarasekara A.S., and Chandrasekara S. Org. Lett. 4 (2002) 773
16. Hwang J.Y., Choi H.S., and Gong Y.D. Tetrahedron Lett. 46 (2005) 3107
17. Dickstein J.I., and Miller S.I. In: Patai S. (Ed). The Chemistry of Functional Groups. The Chemistry of Carbon-Carbon Triple Bonds, Part 2 (1978), Wiley, Chichester Chapter 19, pp. 813-955
18. Nair V., Menon R.S., Sreekanth A.R., Abhilash N., and Biju A.T. Acc. Chem. Res. 39 (2006) 520 and references cited therein
19. Yavari I., Ghazanfarpour-Darjani M., Sabbagan M., and Hossaini Z. Tetrahedron Lett. 48 (2007) 3749
20. Bazgir A., Seyyedhamzeh M., Yasaei Z., and Mirzaei P. Tetrahedron Lett. 48 (2007) 8790
21. Sayyafi M., Seyyedhamzeh M., Khavasi H.R., and Bazgir A. Tetrahedron 64 (2008) 2375
22. Dabiri M., Arvin-Nezhad H., Khavasi H.R., and Bazgir A. J. Heterocycl. Chem. 44 (2007) 1009
23. Dabiri M., Azimi S.C., Arvin-Nezhad H., and Bazgir A. Heterocycles 75 (2008) 87
24. Dabiri M., Delbari A.S., and Bazgir A. Synlett (2007) 821
25. Dabiri M., Arvin-Nezhad H., Khavasi H.R., and Bazgir A. Tetrahedron 63 (2007) 1770
26. Dabiri M., Delbari A.S., and Bazgir A. Heterocycles 71 (2007) 543
27. Seyyedhamzeh M., Mirzaei P., and Bazgir A. Dyes Pigm. 76 (2008) 836