Simple, convenient method for the synthesis of substituted furan-2(5 H)-one derivatives using tin(II) chloride

Synthetic Communications

Volumn 42, Issue 14, 2012, Pages 2139-2148

  Nagarapu, Lingaiah ^a   Kumar, U Nikhil ^a   Upendra, P ^a   Bantu, Rajashaker ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Dimethylacetylenedicarboxylate; furan 2(5 H) ones; three component condensation; tin(II) chloride

Indexed keywords

ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ALDEHYDE; ANILINE; FURAN DERIVATIVE; METHYL 2 (2 CHLOROPHENYL) 2,5 DIHYDRO 5 OXO 4 (PHENYLAMINO) FURAN 3 CARBOXYLATE; METHYL 2 (2 FLUOROPHENYLAMINO) 2,5 DIHYDRO 5 OXO 2 PHENYLFURAN 3 CARBOXYLATE; METHYL 2 (2,4 DICHLOROPHENYL) 2,5 DIHYDRO 5 OXO 4 (PHENYLAMINO) FURAN 3 CARBOXYLATE; METHYL 2 (2,4 DIMETHOXYPHENYL) 2,5 DIHYDRO 5 OXO 4 (PHENYLAMINO) FURAN 3 CARBOXYLATE; METHYL 2 (3 METHOXYPHENYL) 2,5 DIHYDRO 5 OXO 4 (PHENYLAMINO) FURAN 3 CARBOXYLATE; METHYL 2 (4 CHLOROPHENYL) 2,5 DIHYDRO 5 OXO 4 (PHENYLAMINO) FURAN 3 CARBOXYLATE; METHYL 2 (4 FLUOROPHENYLAMINO) 2,5 DIHYDRO 5 OXO 2 PHENYLFURAN 3 CARBOXYLATE; METHYL 2 (4 ISOPROPYLPHENYLAMINO) 2,5 DIHYDRO 5 OXO 2 PHENYLFURAN 3 CARBOXYLATE; METHYL 2 (4 METHOXYPHENYL) 2,5 DIHYDRO 5 OXO 4 (PHENYLAMINO) FURAN 3 CARBOXYLATE; METHYL 2 (4 METHYLPHENYL) 2,5 DIHYDRO 5 OXO 4 (PHENYLAMINO) FURAN 3 CARBOXYLATE; METHYL 2 (4 METHYLPHENYLAMINO) 2,5 DIHYDRO 5 OXO 2 PHENYLFURAN 3 CARBOXYLATE; METHYL 2 (4 TRIFLUOROMETHOXYPHENYLAMINO) 2,5 DIHYDRO 5 OXO 2 PHENYLFURAN 3 CARBOXYLATE; METHYL 2,5 DIHYDRO 5 OXO 2 PHENYL 4 (PHENYLAMINO)FURAN 3 CARBOXYLATE; TIN CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ONE POT SYNTHESIS; POLYMERIZATION; SUBSTITUTION REACTION; THREE COMPONENT CONDENSATION;

EID: 84859183607     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.554062     Document Type: Article

References (25)

1. Rao, Y. S. Recent advances in the chemistry of unsaturated lactones. Chem. Rev. 1976, 76, 625-694.
2. (a) Nemchenko, V. V.; Ivanova, N. P. Humic substances in terrestrial ecosystems. Khim. Sel'sk. Khoz. 1991, 1, 91-93;
3. (b) Aihara, H.; Muramatsu, M.; Arai, I. Jpn Kokai Tokkyo Koho 1988, 225315, 1988;
4. (c) Tsen, L. N.; Suleimanyan, V. S. A convenient synthesis of 2(5H)-furanone. Rybn. Khoz (Moscow) 1982, 5, 37-42;
5. Chem. Abs. 1979, 90, 54751.
6. (a) Massy-Westropp, R. A.; Reynolds, G. D.; Spotswood, T. M. Freelingyne, an acetylenic sequiterpenoid. Tetrahedron Lett. 1966, 7, 1939-1946;
7. (b) Khalid, A.; Sayed, E.; Khaled, Y.; Orabi, D.; Dunbar, C.; Hamann, M. T.; Mitchell, A. A.; Yogesh, A. S.; Jaber, S. M.; El-Feraly, Farouk S. Transformation of lactone to lactam in sarcopine and antimalarial activity of the resulting N-substituted azasarcophines. Tetrahedron 2002, 58, 3699-3708; (Pubitemid 34442530)
8. (c) Ma, S. Shi, Z. Pd(O)=Ag+-cocatalyzed cyclization reaction of 1,2-allenic carboxylic acids with aryl=alkenyl halides: An efficient synthesis of butenolides. J. Org. Chem. 1998, 63, 6387-6389; (Pubitemid 28427616)
9. (d) Alaa, A.; El-Tombary, Y.; Abdel-Ghany, A. S. F. B.; Shams, A.; El-Dine, S.; Farid, S. G. S. Synthesis of some substituted furan-2(5H)-ones and derived quinoxalinones as potential anti-microbial and anticancer agents. Med. Chem. Res. 2011, 20, 865-876.
10. (a) Domschike, G. Z. Chem. 1976, 16, 13;
11. (b) Cao, R.; Liu, C.; Liu, L. A convenient synthesis of 2(5H)-furanone. Org. Prep. Proced. Int. 1996, 28, 215-216;
12. (c) Fu, C.; Ma, S. Efficient preparation of 4-iodofuran-2(5H)-ones by indolactonisation of 2,3-allenoates with I2. Eur. J. Org. Chem. 2005, 3942-3945. (Pubitemid 41323532)
13. Bassetti, M.; D'Annibale, A.; Fanfoni, A.; Minissi, F. Synthesis of a,b-unsaturated 4,5-disubstituted c-lactones via ring-closing metathesis catalyzed by the first-generation Grubb's catalyst. Org. Lett. 2005, 7, 1805-1808. (Pubitemid 40685369)
14. Narayana Murthy, S.; Madhav, B.; Vijay Kumar, A.; Rama Rao, K.; Nageswar, Y. V. D. Facile and efficient synthesis of 3,4,5-substituted furan-2(5H)-ones by using b-cyclodextrin as reusable catalyst. Tetrahedron 2009, 65, 5251-5256.
15. Arumugam, P.; Karthikeyan, G.; Atchutan, R.; Muralidharan, D.; Perumal, P. T. A simple, efficient, and solvent-free protocol for the Friedlander synthesis of quinolines by using SnCl2, 2H2O. Chem. Lett. 2005, 34, 314-315. (Pubitemid 40726560)
16. Yadav, J. S.; Reddy, B. V. S.; Baishya, G.; Reddy, K. V.; Narsaiah, V. Conjugate addition of indoles to a,b-unsaturated ketones using Cu(OTf)2 immobilized in ionic liquids. Tetrahedron 2005, 61, 9541-9544. (Pubitemid 41583473)
17. Da-Gong, G.; Shun-Jun, J.; Zhao-Qin, J.; Min-Feng, Z.; Teck-Peng, L. An efficient synthesis of bis(indolyl) methanes catalyzed by recycled acidic ionic liquid. Synlett. 2005, 959-962.
18. Wang, B., Gu, Y., Luo, C., Yang, T., Yang, L., Suo, J. Pyrrole synthesis in ionic liquids by Pall-Knorr condensation under mild conditions. Tetrahedron Lett. 2004, 45, 3417-3419. (Pubitemid 38471624)
19. Rebeiro, G. L.; Khadilkar, B. M. Chloroaluminate ionic liquid for Fischer indole synthesis. Synthesis 2001, 370-372. (Pubitemid 32217290)
20. (a) Nagarapu, L.; Satyender, A.; Rajashakar, B.; Srinivas, K.; Rupa Rani, P.; Radhika, K.; Subhashini, G. Synthesis and antimicrobial activity of novel C-linked imidazole glycoconjugates. Bioorg. Med. Chem. Lett. 2008, 18, 1167-1171; (Pubitemid 351193006)
21. (b) Nagarapu, L.; Venkateswarlu, P.; Satyender, A. Synthesis of novel analogeues of (+)-varitriol via olefin cross-metathesis reaction. Bioorg. Med. Chem. Lett. 2008, 18, 2351-2354; (Pubitemid 351454033)
22. (c) Nagarapu, L.; Chary, M. V.; Satyender, A.; Supriya, B.; Rajashakar, B. Iron(III) chloride in ethanol-water: Highly efficient catalytic system for the synthesis of Garcia Gonzalez polyhydroxyalkyl-and C-glycosylfurans. Synthesis 2009, 2278-2282;
23. (d) Nagarapu, L.; Narsimhaji, C.; Shukla Chary, K.; Rajashakar, B. Synthesis of annulated pyrroles: Condensation of aldose sugars, arylamines, and 1,3-diones using TBAB. Synthesis 2010, 3374-3378;
24. (e) Nagarapu, L.; Shukla Chary, K.; Rajashakar, B. An efficient, high-yield protocol for the one-pot synthesis of benzopyran derivatives catalyzed by p-TSA in aqueous media. Synth. Commun. 2012, 42, 967-974;
25. (f) Mereyala, H. B.; Pathuri, G.; Nagarapu, L. Synthesis of (2S,4S)-4-hydroxyproline from D-glucose. Synth. Commun. 2012, 42, 1278-1287.