Trichloroacetic acid as a solid heterogeneous catalyst for the rapid synthesis of dihydropyrano[2,3-c]pyrazoles under solvent-free conditions

Heterocyclic Communications

Volumn 17, Issue 5-6, 2011, Pages 177-179

  Karimi Jaberi, Zahed ^a   Shams, Mohammad Mehdi Reyazo ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Aldehyde; Dihydropyranopyrazoles; Malononitrile; Trichloroacetic acid

Indexed keywords

EID: 84856172358     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.2011.046     Document Type: Article

References (21)

1. Abdelrazek, F. M.; Metz, P.; Kataeva, O.; Jaeger, A.; El-Mahrouky, S. F. Synthesis and molluscicidal activity of new chromene and pyrano[2,3-c]pyrazole derivatives. Arch. Pharm. 2007, 340, 543-548. (Pubitemid 350007052)
2. Armetso, D.; Horspool, W. M.; Martin, N.; Ramos, A.; Seaone, C. Synthesis of cyclobutenes by the novel photochemical ring contraction of 4-substituted-2-amino-3,5-dicyano-6-phenyl-4Hpyrans. J. Org. Chem. 1989, 54, 3069-3072.
3. Bonsignore, L.; Loy, G.; Secci, D.; Calignano, A. Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives. Eur. J. Med. Chem. 1993, 28, 517-520. (Pubitemid 23200215)
4. Hatakeyama, S.; Ochi, N.; Numata, H.; Takano, S. A new route to substituted 3-methoxycarbonyldihydropyrans; enantioselective synthesis of (-)-methyl elenolate. J. Chem. Soc. Chem. Commun. 1988, 1202-1204.
5. Heravi, M. M.; Ghods, A.; Derikvand, F.; Bakhtiari, K.; Bamoharram, F. F. H 14 [NaP 5 W 30 O 110] catalyzed one-pot three-component synthesis of dihydropyrano[2,3-c]pyrazole and pyrano [2,3-d] pyrimidine derivatives. J. Iran Chem. Soc. 2010, 7, 615-620.
6. Jin, T. S.; Wang, A. Q.; Cheng, Z. L.; Zhang, J.-S.; Li, T. S. A clean and simple synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4- dihydropyrano[2,3-c]pyrazole in water. Synth. Commun. 2005, 35, 137-143. (Pubitemid 40270844)
7. Jin, T. S.; Zhao, R. Q.; Li, T. S. 14. An one-pot three-component process for the synthesis of amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4- dihydropyrano[2,3-c]pyrazoles in aqueous media. Arkivoc 2006, xi, 176-182.
8. Kamaljit, S. J.; Harjit, S. A synthetic entry into fused pyran derivatives through carbon transfer reactions of 1,3-oxazinanes and oxazolidines with carbon nucleophiles. Tetrahedron 1996, 52, 14273-14280.
9. Karimi-Jaberi, Z.; Amiri, M. One-pot synthesis of α- aminophosphonates catalyzed by boric acid at room temperature. Heteroatom Chem. 2010, 21, 96-98.
10. Karimi-Jaberi, Z.; Keshavarzi, M. Efficient one-pot synthesis of 14-substituted-14H-dibenzo[a,j]xanthenes using boric acid under solvent-free conditions. Chin. Chem. Lett. 2010, 21, 547-549.
11. Karimi-Jaberi, Z.; Amiri, M.; Sadeghi, N. Sodium dihydrogen phosphate as an efficient catalyst for one-pot, three-component synthesis of α-aminophosphonates under solvent-free conditions at room temperature. Synth. Commun. 2010, 40, 2948-2953.
12. Karimi-Jaberi, Z.; Arjmandi, R. Acetic acid-promoted, efficient, onepot synthesis of 2,3-dihydroquinazolin-4(1H)-ones. Monatsh. Chem. 2011, 142, 631-635.
13. Karimi-Jaberi, Z.; Abbasi, S. Z.; Pooladian, B.; Jokar, M. Efficient, one-pot synthesis of tetrahydrobenzo[ a]xanthen-11-ones and dibenzo[a,j] xanthenes using trichloroacetic acid as a solid heterogeneous catalyst under solvent-free conditions. E-J. Chem. 2011, 8, 1895-1899.
14. Khurana, J. M.; Nand, B.; Kumar, S. Rapid synthesis of polyfunctionalized pyrano[2,3-c]pyrazoles via multicomponent condensation in room-temperature ionic liquids. Synth. Commun. 2011, 41, 405-410.
15. Kshirsagar, S. W.; Patil, N. R.; Samant, S. D. Mg-Al hydrotalcite as a first heterogeneous basic catalyst for the synthesis of 4h-pyrano[2,3-c] pyrazoles through a four-component reaction. Synth. Commun. 2011, 41, 1320-1325.
16. Otto, H. H. Darstellung einiger 4H-Pyrano[2,3-c]pyrazolderivate. Arch. Pharm. 1974, 307, 444-447.
17. Otto, H. H.; Schmelz, H. Heterocyclen durch Michael-Reaktionen, 5: mitt. nucleophile additionen an 4-aryliden-pyrazolone. Arch. Pharm. 1979, 312, 478-486. (Pubitemid 9182060)
18. Shi, D.; Mou, J.; Zhuang, Q.; Niu, L.; Wu, N.; Wang, X. Threecomponent one-pot synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivativesin aqueous media. Synth. Commun. 2004, 34, 4557-4563. (Pubitemid 40070237)
19. Thomas, J. M.; Thomas, W. J. Principles and Practice of Heterogeneous Catalysis. Wiley-VCH: Weinhiem, 1997.
20. Witte, E. C.; Neubert, P.; Roesch, A. Ger. Offen. DE 1986, 3427985; 7-(Piperazinylpopoxy)-2H-1-benzopyran-2-ones. Chem. Abstr. 1986, 104, 224915f.
21. Zaki, M. E. A.; Soliman, H. A.; Hiekal, O. A.; Rashad, A. E. Z. Pyrazolopyranopyrimidines as a class of anti-inflammatory agents. Z. Naturforsch. C 2006, 61, 1-5.