A clean and highly efficient synthesis of oxindole substituted pyrrolo[2,3-d]Pyrimidines under ultrasound irradiation

Azimi, Seyyedeh Cobra; Rad-Moghadam, Kurosh

Document Type : Original Research Article

Authors

University of Guilan

Abstract

A practical and new method for the synthesis oxindole substituted pyrrolo[2,3-d]pyrimidines by the condensation of isatin, acetophenone and 6-amino-uracil under ultrasound irradiation conditions at 60 °C was described. The reaction was developed via a sequential tandem process to afford the oxindole substituted pyrrolo[2,3-d]pyrimidines in good to excellent yields. All reactions performed efficiently under ultrasound irradiation and results were compared with conventional heating method. In this field, several types of acetophenones, amino-uracils, and isatins were rapidly changed to the corresponding derivatives. The remarkable features of the new procedure are shorter reaction time, excellent yields, cleaner reaction profile, and simple experimental and workup procedure.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

References

[1] B.M. Trost, Science, 1991, 254, 1471-1477.

[2] T.L. Ho, Tandem Organic Reactions, Wiley: New York, 1992.

[3] L.F. Tietze, F. Hautner, F. Vogtle, J. Stoddart, F.M. Shibasaki, Eds.; Stimulating Concepts in Chemistry, Wiley-VCH: Weinheim, 2000, pp. 38-64.

[4] L.F. Tietze, U. Beifuss, Angew. Chem. Int. Ed. Engl., 1993, 32, 131-163.

[5] L.F. Tietze, Chem. Rev., 1996, 96, 115-136.

[6] P.J. Parsons, C.S. Penkett, A.J. Shell, Chem. Rev., 1996, 96, 195-206.

[7] R.M. McCarty, V. Bandarian, Chem. Biol., 2008, 15, 790-798.

[8] C.E. Muller, I. Hide, J.W. Daly, K. Rothenhausler, K.J. Eger, J. Med.Chem., 1990, 33, 2822-2828.

[9] J. Ford, R.J. Capon, J. Nat. Prod., 2000, 63, 1527-1528.

[10] A. Cutignano, G. Bifulco, I. Bruno, A. Casapullo, L. Gomez-Paloma, R. Riccio, Tetrahedron, 2000, 56, 3743-3748.

[11] S. Olgen, E. Akaho, D. Nebioglu, J. Enzyme Inhib. Med. Chem., 2003, 18, 485-490.

[12] R.M. McCarty, V. Bandarian, Bioorg. Chem., 2012, 43, 15-25.

[13] W.H. Wolberg, Biochem. Pharmacol., 1965, 14, 1921-1925.

[14] E.M. Berman, L.M. Werbel, J. Med. Chem., 1991, 34, 479-485.

[15] Y.H. Koh, J.H. Shim, J.L. Girardet, Z. Hong, Bioorg. Med. Chem. Lett., 2007, 17, 5261-5264.

[16] K. Rao, V. Renn, Antimicrob. Agents Chemother., 1963, 161, 77-79.

[17] S.J. Tangeda, A. Garlapati. Eur. J. Med. Chem., 2010, 45, 1453-1458.

[18] M.S. Mohamed, R. Kamel, S.S. Fatahal, Eur. J. Med. Chem., 2011, 46, 3022-3029.

[19] S.M. Bennett, N.B. Nghe, K.K. Ogilvie, J. Med. Chem., 1990, 33, 2162-2173.

[20] Z. Lian, S.D. Friis, S.D. Skrydstrup, Eur. J. Org. Chem., 2014, 53, 9582-9586.

[21] A.B. Dounay, K. Hatanaka, J.J. Kodanko, M. Oestreich, L.E. Overman, L.A.; Weiss, M.M. Pfeifer, J. Am. Chem. Soc., 2003, 125, 6261-6271.

[22] J. Xue, Y. Zhang, X. Wang, H.K. Fun, J.H. Xu, Org. Lett., 2000, 2, 2583-2586.

[23] J. Dodonova, L. Skardziute, K. Kazlauskas, S. Jursenas, S. Tumkevicius, Tetrahedron 2012, 68, 329-339.

[24] J.T. Gupton, E.J. Banner, A.B. Scharf, B.K. Norwood, R.P.F. Kanters, R.N. Dominey, J.E. Hempel, A. Kharlamova, I. Bluhn-Chertudi, C.R. Hickenboth, B.A. Little, M.D. Sartin, M.B. Coppock, K.E. Krumpe, B.S. Burnham, H. Holt, K.X. Du, K.M. Keertikar, A. Diebes, S. Ghassemid, J.A. Sikorskie, Tetrahedron, 2006, 62, 8243-8255.

[25] T.J. Mason, J.P. Lorimer, Applied Sonochemistry, The Uses of Power Ultrasound in Chemistry and Processing, Wiley VCH, Verlag GmbH, 2002.

[26] T.J. Mason, Ultrason. Sonochem., 2007, 14, 476-483.

[27] T.J. Mason, D. Peters, Practical sonochemistry, second ed.; Ellis Harwood, London, 2002.

[28] G. Cravotto, P. Cintas, Chem. Soc. Rev., 2006, 35, 180-196.

[29] J.M. Lopez-Pestana, M.J. Avila-Rey, R.M. Martin-Aranda, Green Chem., 2002, 4, 628-630.

[30] D.P. Gouvea, D.O.V. Bareno, J. Bosenbecker, B.B. Drawanz, P.D. Neuenfeldt, G.M. Siqueira, W. Cunico, Ultrason. Sonochem., 2012, 19, 1127-1131.

[31] K. Rad-Moghadam, S.C. Azimi, Tetrahedron, 2012, 68, 9706-9712.

[32] K. Rad-Moghadam, S.C. Azimi, J. Mol. Catal. A: Chem., 2012, 363-364, 465-469.

[33] K. Rad-Moghadam, M. Sharifi-Kiasaraie, S.C. Azimi, Tetrahedron, 2012, 68, 6472-6476.

[34] K. Rad-Moghadam, S.C. Azimi, E. Abbaspour-Gilandeh, Tetrahedron Lett., 2013, 54, 4633-4636.

[35] M. Dabiri, S.C. Azimi, H.R. Khavasi, A. Bazgir, Tetrahedron, 2008, 64, 7307-7311.

[36] M. Dabiri, M. Baghbanzadeh, S.C. Azimi, S. Ahmadzadeh-Asl, R. Rezaei Ardestani, Lett. Org. Chem., 2008, 5, 490-494.

[37] R. Ghahremanzadeh, S.C. Azimi, N. Gholami, A. Bazgir, Chem. Pharm. Bull., 2008, 56, 1617-1620.

[38] M. Dabiri, S.C. Azimi, H. Arvin-Nezhad, A. Bazgir, Heterocycles, 2008, 75, 87-93.

[39] S.C. Azimi, H. Kefayati, Iran. J. Catal., 2013, 3, 123-128.

[40] S.C. Azimi, Iran. J. Catal., 2014, 4, 113-120.

[41] S.C. Azimi, Iran. J. Catal., 2013, 3, 21-26.

[42] S.C. Azimi, K. Rad-Moghadam, Iran. Chem. Commun., 2016, 3, 356-366.

[43] S.C. Azimi, E. Abbaspour-Gilandeh, Iran. Chem. Commun., 2016, 4, 245-255.

Iranian chemical communication

A clean and highly efficient synthesis of oxindole substituted pyrrolo[2,3-d]Pyrimidines under ultrasound irradiation

References

References

Volume 5, Issue 2, pp. 121-236, Serial No. 15
April 2017
Pages 156-166

A clean and highly efficient synthesis of oxindole substituted pyrrolo[2,3-d]Pyrimidines under ultrasound irradiation

References

References

Volume 5, Issue 2, pp. 121-236, Serial No. 15April 2017Pages 156-166

Volume 5, Issue 2, pp. 121-236, Serial No. 15
April 2017
Pages 156-166