Abstract
Titanium dioxide nanoparticles were introduced as a new and efficient heterogeneous catalyst for the synthesis of pyran’s annulated heterocyclic systems via three-component reaction. The reaction was carried out between various aldehydes, malononitrile, and cyclic CH-acids in H2O as a green solvent at 50 °C during 10 h. This reaction gave pyrans containing heterocyclic compounds including nineteen derivatives in good yields. Titanium dioxide nanoparticles were recycled and reused for six times without significant decrease in the catalyst amount and efficiency. This approach is very efficient, economical, and environmentally benign process since titanium dioxide is a cheap, available, non-toxic, and recyclable catalyst.
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George SM (1995) Chem Rev 95:475
Nagendrappa G (2002) Resonance 7:59
Simon MO, Li CJ (2012) Chem Soc Rev 41:1415
Grieco PA (1998) Organic synthesis in water. Blackie Academic & Professional, New York
Maldoti A, Molinari A, Amadeni R (2002) Chem Rev 102:3811
Richards R, Li W, Decker S, Davidson C, Koper O, Zaikovski V, Volodin A, Rieker T (2000) J Am Chem Soc 122:4921
Choudary BM, Kantam ML, Ranganath KVS, Mahender K, Sreedhar B (2004) J Am Chem Soc 126:3396
Kantam ML, Laha S, Yadav J, Sreedhar B (2006) Tetrahedron Lett 47:6213
Witte EC, Neubert P, Roesch A (1986) 7-(Piperazinylpropoxy)-2H-1-benzopyran-2-ones. Ger Offen DE 3427985, Jan 30, 1986; (1986) Chem Abstr 104:224915
Uz-zaman S, Siddiqui T, Alam MG, Islam N (2009) Chin Chem Lett 20:153
Bonsignore L, Loy G, Secci D, Calignano A (1993) Eur J Med Chem 28:517
Konkoy CS, Fick DB, Cai SX, Lan NC, Keana JFW (2000) Substituted 5-oxo-5,6,7,8-tetrahydro-4H-1-benzopyrans and benzothiopyrans and their use as potentiators of AMPA. WO 2000075123, Dec 14, 2000; (2000) Chem Abstr 134:29313
Fenn D (ed) (1994) The pyrimidines. Wiley, New York
Ghorab MM, Hassan AY (1998) Phosphorus Sulfur Silicon Relat Elem 141:251
Coates WJ (1990) Preparation of pyrimidopyrimidine derivatives useful as bronchodilators, vasodilators, antiallergic agents, and phosphodiesterase inhibitors. Eur Patent 351058, Jan 17, 1990; (1990) Chem Abstr 113:40711
Davoll J, Clarke J, Elslager EF (1972) J Med Chem 15:837
Levitt G (1982) Herbicidal sulfonamides. US Patent 4339267, Jul 13, 1982; (1983) Chem Abstr 98:215602
Sarrafi Y, Mehrasbi E, Vahid A, Tajbakhsh M (2012) Chin J Catal 33:1486
Baghbanian SM, Rezaei N, Tashakkorian H (2013) Green Chem 15:3446
Joshi VM, Magar RL, Throat PB, Tekale SU, Patil BR, Kale MP, Pawar RP (2014) Chin Chem Lett 25:455
Nemouchi S, Boulcina R, Carboni B, Debache A (2012) C R Chimie 15:394
Edjlali L (2008) J Chin Chem Soc 55:1322
Mirzaei YR, Edjlali L (2010) J Iran Chem Soc 7:685
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We gratefully acknowledge financial support from the Research Council of Tabriz Branch of Islamic Azad University.
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Edjlali, L., Khanamiri, R.H. Titanium dioxide nanoparticles as efficient catalyst for the synthesis of pyran’s annulated heterocyclic systems via three-component reaction. Monatsh Chem 147, 1221–1225 (2016). https://doi.org/10.1007/s00706-015-1624-3
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DOI: https://doi.org/10.1007/s00706-015-1624-3