One-pot three-component reaction of isocyanides, dialkyl acetylenedicarboxylates and phthalhydrazide: synthesis of highly functionalized 1H-pyrazolo[1,2-b]phthalazine-5,10-diones

Tetrahedron

Volumn 62, Issue 47, 2006, Pages 10849-10853

  Teimouri, Mohammad Bagher ^a  

^a IRAN POLYMER AND PETROCHEMICAL INSTITUTE   (Iran)

Author keywords

1H Pyrazolo 1,2 b phthalazine; Dialkyl acetylenedicarboxylate; Isocyanide; Multicomponent reaction; Phthalhydrazide

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; CYANIDE; HYDRAZIDE DERIVATIVE; ISONITRILE DERIVATIVE; PHTHALAZINE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CONJUGATION; ELECTRON; PRIORITY JOURNAL; PROTON TRANSPORT; ROOM TEMPERATURE; SYNTHESIS;

EID: 33749521397     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.006     Document Type: Article

References (58)

1. Franklin E.C. Chem. Rev. 16 (1935) 305-361
2. Bergstrom F.W. Chem. Rev. 35 (1944) 77-277
3. Lichtenthaler F.W. Acc. Chem. Res. 35 (2002) 728-737
4. Litvinov V.P. Russ. Chem. Rev. 72 (2003) 69-85
5. Xu Y., and Guo Q.-X. Heterocycles 63 (2004) 903-974
6. Padwa A., and Waterson A.G. Curr. Org. Chem. 4 (2000) 175-203
7. Orru R.V.A., and de Greef M. Synthesis (2003) 1471-1499
8. Kirsch G., Hesse S., and Comel A. Curr. Org. Chem. 1 (2004) 47-63
9. Vaughan W.R. Chem. Rev. 43 (1948) 447-508
10. Clement R.A. J. Org. Chem. 25 (1960) 1724-1727
11. Heine H.W., Henrie R., Heitz L., and Kovvali S.R. J. Org. Chem. 39 (1974) 3187-3191
12. Heine H.W., Baclawski L.M., Bonser S.M., and Wachob G.D. J. Org. Chem. 41 (1976) 3229-3232
13. Sheradsky T., and Moshenberg R. J. Org. Chem. 51 (1986) 3123-3125
14. Jungheim L.N., and Sigmund S.K. J. Org. Chem. 52 (1987) 4007-4013
15. Indelicato J.M., and Pasini C.E. J. Med. Chem. 31 (1988) 1227-1230
16. Kappe T., and Kos C. Synthesis (1989) 629-630
17. Turk C., Svete J., Stanovnik B., Golič L., Golič-Grdadolnik S., Golobič A., and Selič L. Helv. Chim. Acta 84 (2001) 146-156
18. Clark M.P., Laughlin S.K., Laufersweiler M.J., Bookland R.G., Brugel T.A., Golebiowski A., Sabat M.P., Townes J.A., VanRens J.C., Djung J.F., Natchus M.G., De B., Hsieh L.C., Xu S.C., Walter R.L., Mekel M.J., Heitmeyer S.A., Brown K.K., Juergens K., Taiwo Y.O., and Janusz M.J. J. Med. Chem. 47 (2004) 2724-2727
19. Al'-Assar F., Zelenin K.N., Lesiovskaya E.E., Bezhan I.P., and Chakchir B.A. Pharm. Chem. J. 36 (2002) 598-603
20. Liu B., Brandt J.D., and Moeller K.D. Tetrahedron 59 (2003) 8515-8523
21. Curtis M.D., Hayes N.C., and Matson P.A. J. Org. Chem. 71 (2006) 5035-5038
22. Drew H.D.K., and Hatt H.H. J. Chem. Soc. (1937) 16-26
23. Sinkkonen J., Ovcharenko V., Zelenin K.N., Bezhan I.P., Chakchir B.A., Al-Assar F., and Pihlaja K. Eur. J. Org. Chem. (2002) 2046-2053
24. Sinkkonen J., Ovcharenko V., Zelenin K.N., Bezhan I.P., Chakchir B.A., Al-Assar F., and Pihlaja K. Eur. J. Org. Chem. (2002) 3447-3454
25. Amarasekara A.S., and Chandrasekara S. Org. Lett. 4 (2002) 773-775
26. Winterfeldt E., Schumann D., and Dillinger H.J. Chem. Ber. 102 (1969) 1656-1664
27. Oakes T.R., David H.G., and Nagel F.J. J. Am. Chem. Soc. 91 (1969) 4761-4765
28. Takizawa T., Obata N., Suzuki N., and Yanagida T. Tetrahedron Lett. (1969) 3407-3410
29. Suzuki Y., Otaba N., and Takizawa T. Tetrahedron Lett. (1970) 2667-2670
30. Nair V., Vinod A.U., Abhilash N., Menon R.S., Santhi V., Varma R.L., Viji S., Mathewa S., and Srinivas R. Tetrahedron 59 (2003) 10279-10286
31. Yavari I., and Maghsoodlou M.T. J. Chem. Res., Synop. (1998) 386-387
32. Yavari I., Esmaili A.A., Asghari S., and Bijanzadeh H.R. J. Chem. Res., Synop. (1999) 368-369
33. Yavari I., Hazeri N., Maghsoodlou M.T., and Zabarjad-Shiraz N. Monatsh. Chem. 132 (2001) 683-687
34. Yavari I., Adib M., and Sayahi M.H. J. Chem. Soc., Perkin Trans. 1 (2002) 2343-2346
35. Nair V., Vinod A.U., Ramesh R., Menon R.S., Varma L., Mathew S., and Chiaroni A. Heterocycles 58 (2002) 147-151
36. Maghsoodlou M.T., Yavari I., Nassiri F., Djahaniani H., and Razmjoo Z. Monatsh. Chem. 134 (2003) 1585-1591
37. Yavari I., and Esnaashari M. Synthesis (2005) 1049-1051
38. Asghari S., and Mohammadi L. Tetrahedron Lett. 47 (2006) 4297-4299
39. Teimouri M.B., Bazhrang R., Eslamimanesh V., and Nouri A. Tetrahedron 62 (2006) 3016-3020
40. Shaabani A., Soleimani E., Khavasi H.R., Hoffmann R.-D., Rodewald U.C., and Pöttgen R. Tetrahedron Lett. 47 (2006) 5493-5496
41. Shaabani A., Teimouri M.B., Mirzaei P., and Bijanzadeh H.R. J. Chem. Res., Synop. (2003) 82-83
42. Shaabani A., Teimouri M.B., and Arab-Ameri S. Tetrahedron Lett. 45 (2004) 8409-8413
43. Yavari I., Djahaniani H., and Nassiri F. Monatsh. Chem. 135 (2004) 543-548
44. Adib M., Sayahi M.H., Aghaaliakbari B., and Bijanzadeh H.R. Tetrahedron 61 (2005) 3963-3966
45. Adib M., Ghanbary K., Mostofi M., and Bijanzadeh H.R. Tetrahedron 61 (2005) 2645-2648
46. Adib M., Sayahi M.H., and Rahbari S. Tetrahedron Lett. 46 (2005) 6545-6547
47. Yavari I., Anary-Abbasinejad M., Alizadeh A., and Hossaini Z. Tetrahedron 59 (2003) 1289-1292
48. Yavari I., Djahaniani H., and Nassiri F. Tetrahedron 59 (2003) 9409-9412
49. Yavari I., Djahaniani H., and Nassiri F. Synthesis (2004) 679-682
50. Alizadeh A., Rostamnia S., and Zhu L.-G. Tetrahedron 62 (2006) 5641-5644
51. Teimouri M.B., and Bazhrang R. Bioorg. Med. Chem. Lett. 16 (2006) 3697-3701
52. Shaabani A., Teimouri M.B., Samadi S., and Soleimani K. Synth. Commun. 35 (2005) 535-541
53. Shaabani A., Teimouri M.B., and Bijanzadeh H.R. Monatsh. Chem. 135 (2004) 441-446
54. Shaabani A., Teimouri M.B., and Bijanzadeh H.R. Monatsh. Chem. 135 (2004) 589-593
55. Shaabani A., Teimouri M.B., Bazgir A., and Bijanzadeh H.R. Mol. Diversity 6 (2003) 199-206
56. Shaabani A., and Teimouri M.B. J. Chem. Res., Synop. (2003) 732-733
57. Shaabani A., Teimouri M.B., and Bijanzadeh H.R. Tetrahedron Lett. 43 (2002) 9151-9154
58. Feuer H., Silverman G.B., Angstadt H.P., and Fauke A.R. J. Org. Chem. 27 (1962) 2081-2084