A green one-pot three-component cascade reaction: the synthesis of 2-amino-5,8-dihydro-3H-pyrido[2,3-D]pyrimidin-4-ones in aqueous medium

Molecular Diversity

Volumn 21, Issue 1, 2017, Pages 147-153

  Shaabani, Ahmad ^a   Sepahvand, Heshmatollah ^a   Boroujeni, Mahmoud Borjian ^a   Faroghi, Mohammad Tayeb ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

2, 6 Diaminopyrimidin 4(3H) one; Acetophenone; Dihydropyridopyrimidine; Green synthesis; MCR; Three component reaction

Indexed keywords

2 (AMINO D2 ) 5,7 DIPHENYL 5,8 DIHYDROPYRIDO [2,3 D]PYRIMIDIN 4 (3H)ONE 3,8 D2; 2 AMINO 5 (4 CHLOROPHENYL) 7 PHENYL 5,8 DIHYDROPYRIDO [2,3 D]PYRIMIDIN 4 (3H)ONE; 2 AMINO 5 (4 NITROPHENYL) 7 PHENYL 5,8 DIHYDROPYRIDO [2,3 D]PYRIMIDIN 4 (3H)ONE; 2 AMINO 5 (FURAN 2 YL) 7 PHENYL 5,8 DIHYDROPYRIDO [2,3 D]PYRIMIDIN 4 (3H)ONE; 2 AMINO 5 (NAPHTHALEN 2 YL) 7 PHENYL 5,8 DIHYDROPYRIDO [2,3 D]PYRIMIDIN 4 (3H)ONE; 2 AMINO 5 PHENYL 3,5,6,11 TETRAHYDRO 4H INDENO [2',1':5,6] PYRIDO [2,3 D]PYRIMIDIN 4 ONE; 2 AMINO 5 PHENYL 5,11 DIHYDRO 3H INDENO [2',1':5,6] PYRIDO [2,3 D]PYRIMIDINE 4,6 DIONHE; 2 AMINO 5,7 DIPHENYL 5,8 DIHYDROPYRIDO [2,3 D]PYRIMIDIN 4 (3H)ONE; 2 AMINO 5,8 DIHYDRO 3H PYRIDO [2,3 D]PYRIMIDIN 4 ONE DERIVATIVE; 2 AMINO 7 (4 NITROPHENYL) 5 PHENYL 5,8 DIHYDROPYRIDO [2,3 D]PYRIMIDIN 4 (3H)ONE; 2 AMINO 7 PHENYL 5 (P TOLYL) 5,8 DIHYDROPYRIDO [2,3 D]PYRIMIDIN 4 (3H)ONE; 2 AMINO 7 PHENYL 5 (PYRIDIN 4 YL) 5,8 DIHYDROPYRIDO [2,3 D]PYRIMIDIN 4 (3H)ONE; 2 AMINO 8,8 DIMETHYL 5 PHENYL 5,8,9,10 TETRAHYDROPYRIMIDO [4,5 B]QUINOLINE 4,6 (3H,7H)DIONE; 5,5' (PHENYLMETHYLENE)BIS [2,6 DIAMINOPYRIMIDIN 4 (3H)ONE]; 8 AMINO 5 PHENYL 5,10 DIHYDROPYRIDO[2,3 D:6,5 D']DIPYRIMIDINE 2,4,6 (1H,3H,7H)TRIONE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; ACETOPHENONE; ACETOPHENONE DERIVATIVE; SOLVENT; WATER;

AQUEOUS SOLUTION; ARTICLE; CARBON CARBON BOND; CARBON NITROGEN BOND; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; GREEN CHEMISTRY; MOLECULAR STABILITY; ONE POT THREE COMPONENT CASCADE REACTION; POLYMERIZATION; SYNTHESIS; CATALYSIS; CHEMISTRY;

ACETOPHENONES; CATALYSIS; GREEN CHEMISTRY TECHNOLOGY; PYRIMIDINES; SOLVENTS; WATER;

EID: 85009266125     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-016-9712-9     Document Type: Article

References (35)

1. Mahale S, Bharate SB, Manda S, Joshi P, Bharate SS, Jenkins PR, Vishwakarma RA, Chaudhuri B (2014) Biphenyl-4-carboxylic acid [2-(1H-Indol-3-yl)-ethyl]-methylamide (CA224), a nonplanar analogue of fascaplysin, inhibits Cdk4 and tubulin polymerization: evaluation of in vitro and in vivo anticancer activity. J Med Chem 57:9658–9672. doi:10.1021/jm5014743
2. Nandi S, Bagchi MC (2009) QSAR of aminopyrido[2,3-d]pyrimidin-7-yl derivatives: anticancer drug design by computed descriptors. J Enzyme Inhib Med Chem 24:937–948. doi:10.1080/14756360802519327
3. Barvian M, Boschelli DH, Cossrow J, Dobrusin E, Fattaey A, Fritsch A, Fry D, Harvey P, Keller P, Garrett M (2000) Pyrido[2,3-d]pyrimidin-7-one inhibitors of cyclin-dependent kinases. J Med Chem 43:4606–4616. doi:10.1021/jm000271k
4. ′: 6, 7 ]quinolino[2,3-d]pyrimidine derivatives via three-component microwave-assisted reaction. J Heterocycl Chem 45:1243–1246. doi:10.1002/jhet.5570450452
5. Reck F, Alm RA, Brassil P, Newman JV, Ciaccio P, McNulty J, Barthlow H, Goteti K, Breen J, Comita-Prevoir J (2012) Novel N-linked aminopiperidine inhibitors of bacterial topoisomerase type II with reduced pKa: antibacterial agents with an improved safety profile. J Med Chem 55:6916–6933. doi:10.1021/jm2008826
6. Chaudhari PK (2011) Synthesis and biological studies of trihydropyrido[2,3-d]pyrimidines-6-carbonitrile. Int J Life Sci Pharma Res 1:71–76
7. Ibrahim DA, Ismail NS (2011) Design, synthesis and biological study of novel pyrido[2,3-d]pyrimidine as anti-proliferative CDK2 inhibitors. Eur J Med Chem 46:5825–5832. doi:10.1016/j.ejmech.2011.09.041
8. Srinivasan A, Broom AD (1981) Synthesis of 3-deaza analogs of aminopterin and folic acid. J Org Chem 46:1777–1781. doi:10.1021/jo00322a004
9. Pastor A, Alajarin R, Vaquero JJ, Alvarez-Builla J, de Casa-Juana MF, Sunkel C, Priego JG, Fonseca I, Sanz-Aparicio J (1994) Synthesis and structure of new pyrido[2,3-d]pyrimidine derivatives with calcium channel antagonist activity. Tetrahedron 50:8085–8098. doi:10.1016/S0040-4020(01)85291-1
10. Bagley MC, Dale JW, Bower J (2002) A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines. Chem Commun 1682–1683. doi:10.1039/B203900A
11. Bagley MC, Singh N (2002) Microwave-assisted synthesis of 5-deaza-5,8-dihydropterins. Synlett 2002:1718–1720. doi:10.1055/s-2002-34246
12. Tu S, Zhang J, Zhu X, Xu J, Zhang Y, Wang Q, Jia R, Jiang B, Zhang J (2006) New potential inhibitors of cyclin-dependent kinase 4: Design and synthesis of pyrido[2,3-d]pyrimidine derivatives under microwave irradiation. Bioorg Med Chem Lett 16:3578–3581. doi:10.1016/j.bmcl.2006.03.084
13. Quiroga J, Cisneros C, Insuasty B, Abonía R, Cruz S, Nogueras M, de la Torre JM, Sortino M, Zacchino S (2006) Microwave-assisted three-component synthesis and in vitro antifungal evaluation of 6-cyano-5,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-ones. J Heterocycl Chem 43:299–306. doi:10.1002/jhet.5570430208
14. Tu S, Wang Q, Xu J, Zhu X, Zhang J, Jiang B, Jia R, Zhang Y, Zhang J (2006) An efficient one-pot synthesis of 5-aryl substituted 2-amino-5,8-dihydropyrido[2,3-d]pyrimidin-4,7-diones under microwave irradiation without catalyst. J Heterocycl Chem 43:855–858. doi:10.1002/jhet.5570430407
15. Shi D, Ji S, Niu L, Shi J, Wang X (2007) One-pot synthesis of pyrido[2,3-d]pyrimidines via efficient three-component reaction in aqueous media. J Heterocycl Chem 44:1083–1090. doi:10.1002/jhet.5570440517
16. ′: 5, 6 ]pyrido[2,3-d]pyrimidine derivatives through multicomponent reactions in water. Eur J Org Chem 2007:1522–1528. doi:10.1002/ejoc.200600913
17. Wang X-S, Zhang M-M, Li Q, Yao C-S, Tu S-J (2008) Simple procedure for the synthesis of 5,7-diarylpyrido[2,3-d]pyrimidine derivatives catalyzed by KF-alumina. Synth Commun 38:1896–1908. doi:10.1080/00397910801997488
18. Tu S, Li C, Shi F, Zhou D, Shao Q, Cao L, Jiang B (2008) An efficient chemoselective synthesis of pyrido[2,3-d]pyrimidine derivatives under microwave irradiation. Synthesis 369–376. doi:10.1055/s-2008-1032031
19. Jadidi K, Ghahremanzadeh R, Bazgir A (2009) Spirooxindoles: reaction of 2,6-diaminopyrimidin-4(3H)-one and isatins. Tetrahedron 65:2005–2009. doi:10.1016/j.tet.2009.01.013
20. Shi F, Ding J, Zhang S, Hao W-J, Cheng C, Tu S (2011) Substrate-controlled chemoselective synthesis and potent cytotoxic activity of novel 5,6,7-triarylpyrido[2,3-d]pyrimidin-4-one derivatives. Bioorg Med Chem Lett 21:1554–1558. doi:10.1016/j.bmcl.2010.09.114
21. ′ -indolines. ACS Comb Sci 13:96–99. doi:10.1021/co1000053
22. Shakibaei GI, Feiz A, Bazgir A (2011) A simple and catalyst-free three-component method for the synthesis of spiro[indenopyrazolopyridine indoline]diones and spiro[indenopyridopyrimidine indoline]triones. Comptes Rendus Chim 14:556–562. doi:10.1016/j.crci.2010.10.001
23. ′ -pyrimido[4,5-b]quinoline]-triones in water. J Heterocycl Chem 48:1014–1018. doi:10.1002/jhet.655
24. Shahrzad A, Saeed B (2012) An efficient synthesis of pyrido[2,3-d]pyrimidine derivatives via one-pot three-component reaction in aqueous media. Int J Org Chem 2:7–14. doi:10.4236/ijoc.2012.21002
25. Du BX, Li YL, Wang XS, Shi DQ (2013) Ionic liquid as an efficient and recyclable reaction medium for the synthesis of pyrido[2,3-d]pyrimidines. J Heterocycl Chem 50:534–538. doi:10.1080/00397911.2016.1165254
26. Naeimi H, Rashid Z, Zarnani A-H, Ghahremanzadeh R (2014) MnFe2O4@NH2@2AB-Ni: a novel, highly active, stable and magnetically recoverable nanocatalyst and use of this heterogeneous catalyst in green synthesis of spirooxindoles in water. New J Chem 38:5527–5535. doi:10.1039/C4NJ01182A
27. Naeimi H, Rashid Z, Zarnani AH, Ghahremanzadeh R (2014) Efficient synthesis of novel spiro-furo-pyrido-pyrimidine-indolines by manganese ferrite nanoparticles as a highly active magnetically reusable nanocatalyst in water. New J Chem 38:348–357. doi:10.1039/C3NJ00940H
28. ′:5,6]pyrido[2,3-d]pyrimidine-4,6(3H,5H)-dione derivatives. J Heterocycl Chem 51:163–166. doi:10.1002/jhet.1915
29. Wang J, Li J, Liu H, Xu Z, Zhu S (2015) A facile and efficient synthesis of spiro[indoline-3,5-pyrido[2,3-d]pyrimidine] derivatives via microwave-assisted multicomponent reactions. Lett Org Chem 12:62–66. doi:10.2174/157017861201150112124526
30. DeSimone JM (2002) Practical approaches to green solvents. Science 297:799–803. doi:10.1126/science.1069622
31. Sheldon RA (2005) Green solvents for sustainable organic synthesis: state of the art. Green Chem 7:267–278. doi:10.1039/B418069K
32. Shaabani A, Sepahvand H, Nejad MK (2016) A re-engineering approach: synthesis of pyrazolo[1,2-a]pyrazoles and pyrano[2,3-c]pyrazoles via an isocyanide-based four-component reaction under solvent-free conditions. Tetrahedron Lett 57:1435–1437. doi:10.1016/j.tetlet.2016.02.051
33. Shaabani A, Hooshmand SE, Tabatabaei AT (2016) Synthesis of fully substituted naphthyridines: a novel domino four-component reaction in a deep eutectic solvent system based on choline chloride/urea. Tetrahedron Lett 57:351–353. doi:10.1016/j.tetlet.2015.12.017
34. Shaabani A, Mofakham H, Maleki A, Hajishaabanha F (2010) Novel isocyanide-based one-pot multicomponent syntheses of tetrahydrobenzo[b][1,4]oxazepine and malonamide derivatives. J Comb Chem 12:630–632. doi:10.1021/cc100032d
35. Shaabani A, Rezayan AH, Keshipour S, Sarvary A, Ng SW (2009) A novel one-pot three-(in situ five-) component condensation reaction: an unexpected approach for the synthesis of tetrahydro-2,4-dioxo-1H-benzo[b][1,5]diazepine-3-yl-2-methylpropanamide derivatives. Org Lett 11:3342–3345. doi:10.1021/ol901196z