Eco-efficient ultrasonic responsive synthesis of pyrimidines/pyridines

Ultrasonics Sonochemistry

Volumn 21, Issue 2, 2014, Pages 472-477

  Pagadala, Ramakanth ^a   Maddila, Suresh ^a   Jonnalagadda, Sreekantha B ^a  

^a UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

Multicomponent reaction (MCR); NaOH; Pyrimidine pyridine derivatives; Ultrasound

Indexed keywords

ALDEHYDES; SODIUM HYDROXIDE; ULTRASONICS;

AROMATIC ALDEHYDE; ENVIRONMENT FRIENDLY; FUNCTIONALIZED; MALONONITRILES; MULTI-COMPONENT REACTIONS; MULTICOMPONENTS; SHORT REACTION TIME; ULTRASOUND IRRADIATION;

AROMATIC COMPOUNDS;

ACETANILIDE; ALDEHYDE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; SODIUM HYDROXIDE; THIOUREA;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; ONE POT SYNTHESIS; PRIORITY JOURNAL; ROOM TEMPERATURE; ULTRASOUND;

MULTICOMPONENT REACTION (MCR); NAOH; PYRIMIDINE/PYRIDINE DERIVATIVES; ULTRASOUND;

CHEMISTRY TECHNIQUES, SYNTHETIC; GREEN CHEMISTRY TECHNOLOGY; PYRIDINES; PYRIMIDINES; SODIUM HYDROXIDE; TEMPERATURE; ULTRASONICS;

EID: 84888136636     PISSN: 13504177     EISSN: 18732828     Source Type: Journal    
DOI: 10.1016/j.ultsonch.2013.08.024     Document Type: Article

References (57)

1. C.J. Li Organic reactions in aqueous media with a focus on carbon-carbon bond formation: a decay update Chem. Rev. 105 2005 3095 3166
2. T.M. Potewar, S.A. Ingale, and K.V. Srinivasan Catalyst-free efficient synthesis of 2-aminothiazoles in water at ambient temperature Tetrahedron 64 2008 5019 5022
3. D.N. Zhang, J.T. Li, Y.L. Song, H.M. Liu, and H.Y. Li Efficient one-pot three-component synthesis of N-(4-arylthiazol-2-yl) hydrazones in water under ultrasound irradiation Ultrason. Sonochem. 19 2012 475 478
4. R.S. Varma Solvent-free organic syntheses using supported reagents and microwave irradiation Green Chem. 1 1999 43 55
5. M.J. Lo Fiego, M.A. Badajoz, C. Domini, A.B. Chopa, and M.T. Lockhart Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation Ultrason. Sonochem. 20 2013 826 832
6. W. Chen, and J. Wang Synthesis of pyrrole derivatives from diallylamines by one-pot tandem ring-closing metathesis and metal-catalyzed oxidative dehydrogenation Organometallics 32 2013 1958 1963
7. J.T. Li, G.F. Chen, W.Z. Xu, and T.S. Li The Michael reaction catalyzed by KF/basic alumina under ultrasound irradiation Ultrason. Sonochem. 10 2003 115 118
8. F. Alonso, I.P. Beletskaya, and M. Yus Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 1: the Heck reaction Tetrahedron 61 2005 11771 11835
9. G. Cravotto, G. Palmisano, S. Tollari, G.M. Nano, and A. Penoni The Suzuki homocoupling reaction under high-intensity ultrasound Ultrason. Sonochem. 12 2005 91 94
10. V. Polackova, M. Hutka, and S. Toma Ultrasound effect on Suzuki reactions. 1. Synthesis of unsymmetrical biaryls Ultrason. Sonochem. 12 2005 99 102
11. R. Cella, and H.A. Stefani Ultrasound-assisted synthesis of Z and E stilbenes by Suzuki cross-coupling reactions of organotellurides with potassium organotrifluoroborate salts Tetrahedron 62 2006 5656 5662
12. C. Stavarache, A.M. Procsan, M. Vinatoru, and T.J. Mason A comparison between the sonochemical and thermal reaction Ultrason. Sonochem. 10 2003 49 53
13. K. Peng, F.X. Chen, X.G. She, C.H. Yang, Y.X. Cui, and X.F. Pan Selective oxidation of benzylic or allylic hydroxyl group of sec-1,2-diols Tetrahedron Lett. 46 2005 1217 1220
14. W.-J. Zhou, S.-J. Ji, and Z.-L. Shen An efficient synthesis of ferrocenyl substituted 3-cyanopyridine derivatives under ultrasound irradiation J. Organomet. Chem. 691 2006 1356 1360
15. S.J. Ji, and S.Y. Wang An expeditious synthesis of β-indolylketones catalyzed by p-toluenesulfonic acid (PTSA) using ultrasonic irradiation Ultrason. Sonochem. 12 2005 339 343
16. H. Xu, W.-M. Liao, and H.-F. Li A mild and efficient ultrasound-assisted synthesis of diaryl ethers without any catalyst Ultrason. Sonochem. 14 2007 779 782
17. K.P. Guzen, A.S. Guarezemini, A.T.G. Orfao, R. Cella, C.M.P. Pereiraa, and H.A. Stefani Eco-friendly synthesis of imines by ultrasound irradiation Tetrahedron Lett. 48 2007 1845 1848
18. G. Cravotto, and P. Cintas Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications Chem. Soc. Rev. 35 2006 180 196
19. M.A.P. Martins, C.P. Frizzo, D.N. Moreira, L. Buriol, and P. Machado Solvent-free heterocyclic synthesis Chem. Rev. 109 2009 4140 4182
20. P.W. Cains, P.D. Martin, and C.J. Price The use of ultrasound in industrial chemical synthesis and crystallization-1. Applications to synthetic chemistry Org. Proc. Res. Dev. 2 1998 34 48
21. J. Zhu, and H. Bienaime Multicomponent Reactions 2005 Wiley-VCH Weinheim
22. L.F. Tietze, G. Brasche, and K.M. Gericke Domino Reactions in Organic Synthesis 2006 Wiley-VCH Weinheim
23. 4 at room temperature Tetrahedron Lett. 52 2011 6779 6782
24. V. Nair, C. Rajesh, A.U. Vinod, S. Bindu, A.R. Sreekanth, J.S. Mathen, and L. Balagopal Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes Acc. Chem. Res. 36 2003 899 907
25. J.D. Sunderhaus, and S.F. Martin Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds Chem. Eur. J. 15 2009 1300 1308
26. M. Johar, T. Manning, D.Y. Kunimoto, and R. Kumar Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides Bioorg. Med. Chem. 13 2005 6663 6671
27. N. Azas, P. Rathelot, S. Djekou, F. Delmas, A. Gellis, C. Di Giorgio, P. Vanelle, and P. Timon-David Antiparasitic activity of highly conjugated pyrimidine-2,4-dione derivatives Il Farmaco 58 2003 1263 1270
28. A. Agarwal, K. Srivastava, S.K. Puri, and P.M.S. Chauhan Synthesis of 2,4,6-trisubstituted pyrimidines as antimalarial agents Bioorg. Med. Chem. 13 2005 4645 4650
29. N.R. Kamdar, D.D. Haveliwala, P.T. Mistry, and S.K. Patel Design, synthesis and in vitro evaluation of antitubercular and antimicrobial activity of some novel pyranopyrimidines Eur. J. Med. Chem. 45 2010 5056 5063
30. O. Bruno, C. Brullo, A. Ranise, S. Schenone, F. Bondavalli, E. Barocelli, V. Ballabeni, M. Chiavarini, M. Tognolini, and M. Impicciatore Synthesis and pharmacological evaluation of 2,5-cycloamino-5H-[1]benzopyrano[4,3-d]pyrimidines endowed with in vitro antiplatelet activity Bioorg. Med. Chem. Lett. 11 2001 1397 1400
31. K.C. Majumdar, and S.K. Chattopadhyay Synthesis of pyrimidine annulated furothiopyrans: An efficient sequential and tandem catalyzed Claisen rearrangement, intramolecular hydroaryloxylation Can. J. Chem. 84 2006 469 475
32. K.C. Majumdar, N.K. Jana, A. Bandyopadhyay, and S.K. Ghosh Synthesis of pyrimidine-annelated heterocycles: thermal rearrangement of 1,3-dimethyl-5- (prop-2-enylthio)-pyrimidine-2,4-diones Synth. Commun. 31 2001 2979 2985
33. T. Hanket, R.M. Brunne, H. Miller, and F. Reichel Statistical investigation into the structural complementarity of natural products and synthetic compounds Angew. Chem. Int. Ed. 38 1999 643 647
34. A.V. Rama Rao, G. Ravindra Reddy, and B. Venkateswara Rao Stereoselective synthesis of theonelladins A-D J. Org. Chem. 56 1991 4545 4547
35. L. Jayasinghe, C.P. Jayasooriya, N. Hara, and Y. Fujimoto A pyridine ring-containing ecdysteroid from Diploclisia glaucescens Tetrahedron Lett. 44 2003 8769 8771
36. G.D. Henry De novo synthesis of substituted pyridines Tetrahedron 60 2004 6043 6061
37. T. Kubota, T. Nishi, E. Fukushi, J. Kawabata, J. Fromont, and J. Kobayashi Nakinadine A, a novel bis-pyridine alkaloid with a β-amino acid moiety from sponge Amphimedon sp Tetrahedron Lett. 48 2007 4983 4985
38. B.B. Fredholm, A.P. Ijzerman, K.A. Jacobson, K.N. Klotz, and J. Linden Pharmacol. Rev. 53 2001 527 552
39. D. Matthew Hill, recent strategies for the synthesis of pyridine derivatives Chem. Eur. J. 16 2010 12052 12062
40. D. Alexander, W. Wang, and K. Wang Chemistry and Biology of multicomponent reactions Chem. Rev. 112 2012 3083 3135
41. T.P. Selvam, C.R. James, P.V. Dniandev, and S.K. Valzita A mini review of pyrimidine and fused pyrimidine marketed drugs Res. Pharm. 2 4 2012 01 09
42. C.O. Kappe, and P. Roschger Synthesis and reactions of "biginelli-compounds". Part I J. Heterocycl. Chem. 26 1989 55 64
43. A. Mobinikhaledi, N. Foroughifar, and F. Goodarzi Synthesis of some bicyclic thiazolo and thiazepinopyrimidine derivatives Phosphorus, Sulfur, Silicon Relat. Elem. 179 2004 507 512
44. A. Mobinikhaledi, N. Foroughifar, and B. Ahmadi Synthesis of some bicyclic thiazolo- and oxothiazolo-pyrimidines Phosphorus, Sulfur, Silicon Relat. Elem. 180 2005 339 345
45. J.D. Akbari, P.K. Kachhadia, S.D. Tala, A.H. Bapodra, M.F. Dhaduk, H.S. Joshi, K.B. Mehta, and S.J. Pathak Synthesis of some new 1,2,3,4- tetrahydropyrimidine-2-thiones and their thiazolo[3,2-a]pyrimidine derivatives as potential biological agents Phosphorus, Sulfur, Silicon Relat. Elem. 183 2008 1911 1922
46. M.M. Heravi, S. Sadjadi, H.A. Oskooie, R.H. Shoar, and F.F. Bamoharram A direct oxidative route for the synthesis of pyrimidines using heteropolyacids Tetrahedron Lett. 50 2009 662 666
47. Z.H. Ren, Z.Y. Zhang, B.Q. Yang, Y.Y. Wang, and Z.H. Guan Org. Lett. 13 2011 5394 5397
48. Y. Zou, Q. Liu, and A. Deiters Synthesis of the pyridine core of cyclothiazomycin Org. Lett. 13 2011 4352 4355
49. N.M. Evdokimov, I.V. Magedov, A.S. Kireev, and A. Kornienko One-step, three-component synthesis of pyridines and 1,4-dihydropyridines with manifold medicinal utility Org. Lett. 8 2006 899 902
50. Md. Nasim Khan, S. Pal, T. Parvin, and L.H. Choudhury A simple and efficient method for the facile access of highly functionalized pyridines and their fluorescence property studies RSC Adv. 2 2012 12305 12314
51. T.J. Mason Ultrasound in synthetic organic chemistry Chem. Soc. Rev. 26 1997 443 451
52. S. Maddila, P. Lavanya, K. Naga Raju, S.B. Jonnalagadda, and C. Venkata Rao Synthesis and biological studies of novel 2-(4-substitutedbenzylthio)-5- amino-6-(benzo[d]thiazol-2-yl)-7-(4-chlorophenyl)pyrido[2,3-d]-pyrimidin-4(3H) -one Org. Commun. 4 2011 33 41
53. S. Maddila, and S.B. Jonnalagadda New class of triazole derivatives and their antimicrobial activity Lett. Drug Des. Discovery 9 2012 687 693
54. S. Maddila, and S.B. Jonnalagadda Synthesis of new 1,3,4-thiadiazoles containing oxadiazole, thiadiazole and triazole nuclei and their antimicrobial activity Pharma. Chem. J. 46 2013 1 6
55. R. Pagadala, S.M. Jyotsna, N.C. Himani, and P. Nagender Reddy A zeolite promoted expeditious one-pot synthesis of 1-Arylmethyl-4,5-dihydro-2-aryl-1H- imidazole J. Het. Chem. 47 2010 350 353
56. P. Ramakanth, S.M. Jyotsna, N.C. Himani, J. Venkateshwarlu, K. Uppalaiah, and V. Udayini Prediction of theoretical physicochemical properties and one-pot synthesis of bis-azetidinones by [2 + 2] ketene-imine cycloaddition in the presence of montmorillonite Med. Chem. 7 2011 325 332
57. J.L. Luche, C. Einhorn, J. Einhorn, and J.V. Sinisterra-Gago Organic sonochenistry: a new interpretation and its consequences Tetrahedron Lett. 31 29 1990 4125 4128