Citation: Mohamed A. Ameen, Sara M. Motamed, Fathy F. Abdel-latif. Highly efficient one-pot synthesis of dihydropyran heterocycle[J]. Chinese Chemical Letters, ;2014, 25(2): 212-214. shu

Highly efficient one-pot synthesis of dihydropyran heterocycle

1.
Chemistry Department, Faculty of Science, El Minia University, El Minia 61511, Egypt

Corresponding author: Mohamed A. Ameen,
Received Date: 9 June 2013
Available Online: 13 November 2013

Diammonium hydrogen phosphate and potassium carbonate-catalyzed one-pot synthesis of 1,4-phenylene-bis(2-amino-4H-pyran-3-carbonitrile and 2-amino-4-aryl-4H-pyran-3-carbonitrile derivatives has been achieved by a three-component cyclocondensation of aldehydes, malononitrile, and different nucleophiles in aqueous medium in high yields.
- One pot synthesis,
- Diammonium hydrogen phosphate,
- Pyran,
- Aqueous media
1. [1]
  [1] (a) D.F. Lu, Y.J. Li, Y.F. Gong, Organocatalytic asymmetric tandem Michael addition- hemiacetalization: a route to chiral dihydrocoumarins, chromanes, and 4Hchromenes, J. Org. Chem. 75 (2010) 6900-6907; (b) A.V. Stachulski, N.G. Berry, A.C.L. Low, et al., Identification of isoflavone derivatives as effective anticryptosporidial agents in vitro and in vivo, J. Med. Chem. 49 (2006) 1450-1454; (c) M.N. Elinson, A.S. Dorofeev, F.M. Miloserdov, et al., Catalysis of salicylaldehydes and two different C-H acids with electricity: first example of an efficient multicomponent approach to the design of functionalized medicinally privileged 2-amino-4H-chromene scaffold, Adv. Synth. Catal. 350 (2008) 591-601.
2. [2]
  [2] (a) L. Bonsignore, G. Loy, D. Secci, A. Calignano, Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives, Eur. J. Med. Chem. 28 (1993) 517-520; (b) K. Terao, E. Niki, Damage to biological tissues induced by radical initiator 2,2'- azobis(2-amidinopropane) dihydrochloride and its inhibition by chain-breaking antioxidants, J. Free Radic. Biol. Med. 2 (1986) 193-201; (c) D.J. Maloney, S.M. Hecht, A stereocontrolled synthesis of δ-trans-tocotrienoloic acid, Org. Lett. 7 (2005) 4297-4300.
3. [3]
  [3] W. Kemnitzer, J. Drewe, S. Jiang, et al., Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell-and caspase-based high-throughput screening assay. 1. Structure-activity relationships of the 4-aryl group, J. Med. Chem. 47 (2004) 6299-6310.
4. [4]
  [4] X.S. Wang, D.Q. Shi, Y.F. Zhang, S.H. Wang, S.J. Tu, Synthesis of 9-arylpolyhydroacridine in water catalyzed by triethylbenzylammonium chloride (TEBA), Chin. J. Org. Chem. 24 (2004) 430.
5. [5]
  [5] Merck Catalogue of Chemical Reagents, 2006-2007, Cat. No. 101206.
6. [6]
  [6] (a) R.J. Lewis, Hawley's Condensed Chemical Dictionary, 13th ed., Van Nostrand Reinhold, New York, 1997; (b) J.I. Kroschwitz, A. Seidel, 3rd ed., Kirk-Othmer Encyclopedia of Chemical Technology, 10, John Wiley, New York, 1980, pp. 93-97.
7. [7]
  [7] P. Salehi, M. Dabiri, A.R. Khosropour, P.J. Roozbehniya, Diammonium hydrogen phosphate: a versatile and inexpensive reagent for one-pot synthesis of dihydropyrimidinones, quinazolinones, and azalactones under solvent-free conditions, Iranian Chem. Soc. 3 (2006) 98-104.
8. [8]
  [8] S. Balalaie, M. Bararjanian, S. Hekmat, P. Salehi, Novel, efficient, and green procedure for the Knoevenagel condensation catalyzed by diammonium hydrogen phosphate in water, Synth. Commun. 36 (2006) 2549-2557.
9. [9]
  [9] (a) S. Balalaie, A. Arabanian, One-pot synthesis of tetrasubstituted imidazoles catalyzed by zeolite HY and silica gel under microwave irradiation, Green Chem. 2 (2000) 274-276; (b) S. Balalaie, E. Kowsari, One-pot synthesis of N-substituted 4-aryl-1,4-dihydropyridines under solvent-free conditions and microwave irradiation, Monatsh Chem. 132 (2001) 1551-1555; (c) S. Balalaie, E. Kowsari, M.S. Hashtroudi, An efficient method for the synthesis of 3-cyano-6-hydroxy-2(1H)-pyridinones under microwave irradiation and solvent- free conditions, Monatsh Chem. 134 (2003) 453-456.
10. [10]
  [10] R.M. Shaker, Synthesis and reactions of some new 4H-pyranol[3,2-C]benzopyran- 5-one derivatives and their potential biological activities, Pharmazie 51 (1996) 148-151.
11. [11]
  [11] Y.J. Feng, C.B. Miao, Y. Gao, et al., Dialdehyde in heterocyclic synthesis: synthesis of compounds containing two 4H-benzopyran building blocks under microwave irradiation, Chin. J. Chem. 22 (2004) 622-626.
12. [12]
  [12] F.F. Abdel-Latif, M.M. Mashaly, R. Mekheimer, T.B.Z. Abdel-Aleem, Heterocycle syntheses through ternary condensation of terephthalaldehyde with malononitrile and some nucleophiles, Z. Naturforsch. 48b (1993) 817.
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沈阳化工大学材料科学与工程学院沈阳 110142