SYNTHESIS OF PYRANO[2,3-d] PYRIMIDINONE
185
5. Bonsignore, L., Loy, G., Secci, D., and Calignano, A. Synthesis and pharma-
cological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives.
Eur. J. Med. Chem. 1983, 28, 517–520.
20. Gao, Y., Tu, S. J., Li, T., Zhang, X., Zhu, S., Fang, F., and Shi, D. Ef-
fective synthesis of 7-amino-6-cyano-5-aryl-5H-pyrano[2,3-d]pyrimidine-
2,4(1H,3H)-diones under microwave irradiation. Synth. Commun. 2004,
34, 1295–1299.
6. Wang, X.S., Shi, D.Q., Tu, S.T., and Yao, C.S. A convenient synthesis
of 5-oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran derivatives catalyzed by 21. Devi, I., Kumar, B. S. D., and Bhuyan, P. J. A novel three-component one-
KF-alumina. Synth. Commun. 2003 , 33, 119–126.
7. Tu, S.J., Gao, Y., Guo, C., Shi, D., and Lu, Z. A convenient synthe-
sis of 2-amino-5,6,7,8-tetrahydro-5-oxo-4-aryl-7,7-dimethyl-4H-benzo-
pot synthesis of pyrano[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines
using microwave heating in the solid state. Tetrahedron Lett. 2003, 44,
8307–8310.
[b]-pyran-3-carbonitrile under microwave irradiation. Synth. Commun. 22. Balalaie, S., Abdolmohammadi, Sh., Bijanzadeh, H. R., and Amani, A. M.
2002, 32, 2137–2141.
8. Li, J.T., Xu, W.Z., Yang, L.C., and Li, T.S. One-pot synthesis of 2-amino-
4-aryl-3-carbalkoxy-7,7-dimethyl-5,6,7,8-tetrahydrobenzo[b]pyran deriva-
Diammonium hydrogen phosphate as a versatile and efficient catalyst for
the one-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives in aqueous
media. Mol. Divers. 2008, 12, 85–91.
tives catalyzed by KF/Basic Al2O3 under ultrasound irradiation. Synth. 23. Bararjanian, M., Balalaie, S., Movassagh, B., and Amani, A.M. One-pot
Commun. 2004, 34, 4565–4571.
9. Jin, T.S., Wang, A.Q., Wang, X., Zhang, J.S., and Li, T.S. A clean one-
synthesis of pyrano[2,3-d]pyrimidinone derivatives catalyzed by L-proline
in aqueous media. J. Iran. Chem. Soc. 2009, 6, 436–442.
pot synthesis of tetrahydrobenzo[b]pyran derivatives catalyzed by cexade- 24. Azizian, J., Mohammadi, A.A., Bidar, I., and Mirzaei, P. KAl(SO4)2.12H2O
cyltrimethyl ammonium bromide in aqueous media. Synlett, 2004, 871–873.
10. Shi, D.Q., Zhang, S., Zhuang, Q.Y., Tu, S.J., and Hu, H.W., Clean synthe-
sis of 2-amino-3-cyano-4-aryl-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydro-
benzo[b]pyran in water. Chin. J. Org. Chem. 2003, 23, 877–879.
11. Peng, Y., and Song, G. Amino-functionalized ionic liquid as catalytically
active solvent for microwave-assisted synthesis of 4H-pyrans. Catal. Com-
mun. 2007, 8, 111–114.
(alum) a reusable catalyst for the synthesis of some 4-substituted coumarins
via Pechmann reaction under solvent-free conditions. Monatsh. Chem.
2008, 139, 805–808.
25. Mohammadi, A.A., Dabiri, M., and Qaraat, H. A regioselective three-
component reaction for synthesis of novel 1ꢀH-spiro[isoindoline-1,2ꢀ-
quinazoline]-3,4ꢀ(3ꢀH)-dione derivatives. Tetrahedron, 2009, 65, 3804–
3808.
12. Hekmatshoar, R., Mojedi, S., and Bakhtiari, Kh. Sodium selenate cat-
alyzed simple and efficient synthesis of tetrahydrobenzo[b]pyran deriva-
tives. Catal. Commun. 2008, 9, 307–310.
26. Mohammadi, A.A., Mivechi, M., and Kefayati, H. Potassium aluminum sul-
fate (alum): An efficient catalyst for the one-pot synthesis of trisubstituted
imidazoles. Monatsh. Chem. 2008, 139, 935–937.
13. Balalaie, S., Bararjanian, M., Amani, A. M., and Movassagh, B. (S)-proline 27. Azizian, J., Mohammadi, A.A., Karimi, A.R., and Mohammadizadeh, M.R.
as a neutral and efficient catalyst for the one-pot synthesis of tetrahydro-
break benzo[b]pyran derivatives in aqueous media. Synlett, 2006, 263–266.
14. Balalaie, S., Sheikh-Ahmadi, M., and Bararjanian, M. Tetra-methyl ammo-
nium hydroxide: An efficient and versatile catalyst for the one-pot synthesis
KAl(SO4)2·12HO supported on silica gel as a novel heterogeneous system
catalyzed biginelli reaction: One-pot synthesis of di-hydropyrimidinones
under solvent-free conditions. Applied Catalysis A: General, 2006, 300,
85–88.
of tetrahydrobenzo[b]pyran derivatives in aqueous media. Catal. Commun. 28. Mahajan, D., Naqvi, T., Sharma, R.L., and Kapoor, K.K., Alum-catalyzed
2007, 8, 1724–1728.
15. Lian, X. Z., Huang, Y., Li, Y. Q., and Zheng, W. J. A green synthesis
one-pot solventless synthesis of 1,5-benzodiazepines. Australian Journal
of Chemistry, 2008, 61, 159–162.
of tetrahydrobenzo[b]pyran derivatives through three-component conden- 29. Foroughifar, N., Mobinikhaledi, A., Moghanian, H., Ebrahimi, S., and
sation using N-methylimidazole as organocatalyst. Monatsh. Chem. 2008,
139, 129–131.
16. Grivsky, E.M., Lee, S., Sigel, C.W., Duch, D.S., and Nichol, C.A. Syn-
thesis and antitumor activity of 2,4-diamino-6-(2,5-dimethoxybenzyl)-5-
methylpyrido[2,3-d]pyrimidine. J. Med. Chem. 1980, 23, 327–329.
17. Ghorab, M.M., and Hassan, A.A. Synthesis and antibacterial properties
Bodaghi Fard, M. A. A novel efficient four- and five-component, one-pot
synthesis of 4-semicarbazonoalkyl-2-naphthols. Synlett, 2008, 821–826.
30. Foroughifar, N., Mobinikhaledi, A., Bodaghi Fard, M. A., Moghanian, H.,
and Ebrahimi, S. Sulfamic acid catalyzed one-pot synthesis of polyhydro-
quinolines via the Hantzsch four component condensation reaction.Synth.
React. Inorg. M. 2009, 39, 161–164.
of new dithienyl containing pyran, pyrano[2,3-b] pyridine, pyrano[2,3- 31. Foroughifar, N., Mobinikhaledi, A., and Moghanian, H., Simple and effi-
d]pyrimidine and pyridine derivatives. Phosphorus, Sulfur, Silicon & Re-
lated Elem. 1998, 141, 251–261.
18. Davoll, J., Clarke, J., and Elslager, E. F. Antimalarial and antimetabolite ef-
fects of 2,4-diamino-6-[(benzyl)amino]pyrido [2,3-d]-pyrimidines. J. Med.
Chem. 1972, 15, 837–839.
cient method for synthesis of novel 4-substituted 1-acylthiosemicarbazides
via one-pot multicomponent reactions. Synth. Commun. 2009, 39, 3668–
3676.
32. Foroughifar, N., Mobinikhaledi, A., and Moghanian, H., A catalytic
and green procedure for synthesis of 12-aryl- or 12-alkyl-8,9,10,12-
tetrahydrobenzo[α]xanthen-11-one derivatives under solvent-Free condi-
tions. Int. J. Green Nano.: Phys. Chem. 2009, 1, 57–63.
19. Kretzschmar, E. On derivatives of 4-oxo-3,4-dihydropyrido[2,3-
d]pyrimidine. Pharmazie, 1980, 35, 253–256.