Spirooxindoles: reaction of 2,6-diaminopyrimidin-4(3H)-one and isatins

Tetrahedron

Volumn 65, Issue 10, 2009, Pages 2005-2009

  Jadidi, Khosrow ^a   Ghahremanzadeh, Ramin ^a   Bazgir, Ayoob ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

2,6 Diaminopyrimidin 4(3H) one; Isatin; Spiro pyrimidoquinoline pyrrolopyrimidine ; Spirooxindole

Indexed keywords

2',8' DIAMINO 5 BROMO SPIRO(1 ETHYLINDOLINE 3,5' PYRIDO[2,3 D:6,5 D']DIPYRIMIDINE) 2,4',6'(3'H,7'H,10'H ) TRIONE; 2',8' DIAMINO 5 BROMO SPIRO(1 METHYLINDOLINE 3,5' PYRIDO[2,3 D:6,5 D']DIPYRIMIDINE) 2,4',6'(3'H,7'H,10'H) TRIONE; 2',8' DIAMINO 5 NITRO SPIRO(1 ETHYLINDOLINE 3,5' PYRIDO[2,3 D:6,5 D']DIPYRIMIDINE) 2,4',6'(3'H,7'H,10'H) TRIONE; 2',8' DIAMINO 5 NITRO SPIRO(1 METHYLINDOLINE 3,5' PYRIDO[2,3 D:6,5 D']DIPYRIMIDINE) 2,4',6'(3'H,7'H,10'H) TRIONE; 2',8' DIAMINO SPIRO(1 BENZYLINDOLINE 3,5' PYRIDO[2,3 D:6,5 D']DIPYRIMIDINE) 2,4',6'(3'H,7'H,10'H) TRIONE; 2',8' DIAMINO SPIRO(1 ETHYLINDOLINE 3,5' PYRIDO[2,3 D:6,5 D']DIPYRIMIDINE) 2,4',6'(3'H,7'H,10'H) TRIONE; 2',8' DIAMINO SPIRO(1 METHYLINDOLINE 3,5' PYRIDO[2,3 D:6,5 D']DIPYRIMIDINE) 2,4',6'(3'H,7'H,10'H) TRIONE; 2,2' DIAMINO 3H SPIRO(PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE) 4,4',6'(3'H,7'H,10H) TRIONE; 2,2' DIAMINO 7 BROMO 3H SPIRO(PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE) 4,4',6'(3'H,7'H,10H) TRIONE; 2,2' DIAMINO 7 METHYL 3H SPIRO(PYRIMIDO[4,5B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE) 4,4',6'(3'H,7'H,10H) TRIONE; 2,2' DIAMINO 7 NITRO 3H SPIRO(PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE) 4,4',6'(3'H,7'H,10H) TRIONE; ALCOHOL; INDOLE DERIVATIVE; ISATIN DERIVATIVE; PYRIMIDINONE DERIVATIVE; SPIRO(INDOLINE PYRIMIDO[2,3 D:6,5 D']DIPYRIMIDINE) DERIVATIVE; SPIRO(PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE) DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL;

EID: 59449085073     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.01.013     Document Type: Article

References (31)

1. Dömling A., and Ugi I. Angew. Chem., Int. Ed. 39 (2000) 3168
2. Dömling A. Chem. Rev. 106 (2006) 17
3. Hossain N., Rozenski J., Clercq E.D., and Herdewijn P. J. Org. Chem. 62 (1997) 2442
4. Sabnis R.W., and Rangnekar D.W. Indian J. Technol. 28 (1990) 54
5. Joseph S., and Burke J.M. J. Biol. Chem. 268 (1993) 24515
6. Bookser B.C., Ugarkar B.G., Matelich M.C., Lemus R.H., Allan M., Tsuchiya M., Nakane M., Nagahisa A., Wiesner J.B., and Erion M.D. J. Med. Chem. 48 (2005) 7808
7. Wang S., Folkes A., Chuckowree I., Cockcroft X., Sohal S., Miller W., Milton J., Wren S.P., Vicker N., Depledge P., Scott J., Smith L., Jones H., Mistry P., Faint R., Thompson D., and Cocks S. J. Med. Chem. 47 (2004) 1329
8. Bruno O., Brullo C., Schenone S., Bondavalli F., Ranise A., Tognolini M., Impicciatore M., Ballabeni V., and Barocelli E. Bioorg. Med. Chem. 14 (2006) 121
9. Sannigrahi M. Tetrahedron 55 (1999) 9007
10. Srivastav N., Mittal A., and Kumar A. J. Chem. Soc., Chem. Commun. (1992) 493
11. James D.M., Kunze H.B., and Faulkner D.J. J. Nat. Prod. 54 (1991) 1137
12. Kobayashi J., Tsuda M., Agemi K., Shigemiri H., Ishibashi M., Sasaki T., and Mikami Y. Tetrahedron 47 (1991) 6617
13. Williams R.M., and Cox R.J. Acc.Chem. Res. 36 (2003) 127
14. Da Silva J.F.M., Garden S.J., and Pinto A.C. J. Braz. Chem. Soc. (2001) 273
15. Yong S.R., Ung A.T., Pyne S.G., Skelton B.W., and White A.H. Tetrahedron 63 (2007) 1191
16. Marti C., and Carreira E.M. J. Am. Chem. Soc. 127 (2005) 11505
17. Jiang T., Kuhen K.L., Wolff K., Yin H., Bieza K., Caldwell J., Bursulaya B., Wu T.Y.-H., and He Y. Bioorg. Med. Chem. Lett. 16 (2006) 2105
18. Robertson D.W., Krushinski J.H., Pollock G.D., Wilson H., Kauffman R.F., and Hayes J.S. J. Med. Chem. 30 (1987) 824
19. Yong S.R., Williams M.C., Pyne S.G., Ung A.T., Skelton B.W., White A.H., and Turner P. Tetrahedron 61 (2005) 8120
20. Feldman K.S., Vidulova D.B., and Karatjas A.G. J. Org. Chem. 70 (2005) 6429
21. Osman F.H., and El-Samahy F.A. Tetrahedron 56 (2000) 1863
22. Mao Z., and Baldwin S.W. Org. Lett. 6 (2004) 2425
23. Feldman K.S., and Karatjas A.G. Org. Lett. 8 (2006) 4137
24. Dabiri M., Azimi S.C., Khavasi H.R., and Bazgir A. Tetrahedron 64 (2008) 7307
25. Bazgir A., Seyyedhamzeh M., Yasaei Z., and Mirzaei P. Tetrahedron Lett. 48 (2007) 8790
26. Sayyafi M., Seyyedhamzeh M., Khavasi H.R., and Bazgir A. Tetrahedron 64 (2008) 2375
27. Dabiri M., Arvin-Nezhad H., Khavasi H.R., and Bazgir A. J. Heterocycl. Chem. 44 (2007) 1009
28. Dabiri M., Azimi S.C., Arvin-Nezhad H., and Bazgir A. Heterocycles 75 (2008) 87
29. Dabiri M., Delbari A.S., and Bazgir A. Synlett (2007) 821
30. Dabiri M., Arvin-Nezhad H., Khavasi H.R., and Bazgir A. Tetrahedron 63 (2007) 1770
31. Dabiri M., Delbari A.S., and Bazgir A. Heterocycles 71 (2007) 543