Reaction between 1,3-dicarbonyl-containing CH acids and dialkyl acetylenedicarboxylates in the presence of silica gel in solvent-free conditions: An efficient method for the synthesis of electron-poor alkenes and pyranes

Synthetic Communications

Volumn 39, Issue 7, 2009, Pages 1204-1214

  Ramazani, Ali ^a   Noshiranzadeh, Nader ^a  

^a UNIVERSITY OF ZANJAN   (Iran)

Author keywords

1,3 diketone; Acetylenic ester; CH acid; Electron poor alkene; Pyrane; Silica gel; Solvent free conditions

Indexed keywords

5 ETHYL 4 METHYL 6 METHYL 2 OXO 2H PYRAN 4,5 DICARBOXYLATE; ALKENE DERIVATIVE; DIETHY2 (1 BENZOYL 2 OXO 2 PHENYLETHYLIDENE)SUCCINATE; DIETHYL 2 [1 BENZOYL 2 HYDROXY 2 PHENYL 1 ETHYENYL] 2 BUTENEDIOATE; DIMETHYL 2 (1 BENZOYL 2 OXO 2 PHENYLETHYLIDENE)SUCCINATE; DIMETHYL 2 [1 (2,2 DIMETHYLPROPANOYL) 3,3 DIMETHYL 2 OXOBUTYL] 2 BUTENEDIOATE; DIMETHYL 2 [1 ACETYL 2 HYDROXY 1 PROPENYL] 2 BUTENEDIOATE; DIMETHYL 2 [1 BENZOYL 2 HYDROXY 2 PHENYL 1 ETHYENYL] 2 BUTENEDIOATE; ETHYL 5 BENZOYL 2 OXO 6 PHENYL 2H PYRAN 4 CARBOXYLATE; ETHYL 5 BENZOYL 6 ETHYL 2 OXO 2H PYRAN 4 CARBOXYLATE; METHYL 5 BENZOYL 6 METHYL 2 OXO 2H PYRAN 4 CARBOXYLATE; PYRAN DERIVATIVE; SILICON DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 61949315966     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802517830     Document Type: Article

References (21)

1. Deka, N.; Mariotte, A.-M.; Boumendjel, A. Microwave mediated solvent-free acetylation of deactivated and hindered phenols. Green Chem. 2001, 3, 263-264.
2. 3. Green Chem. 2001, 3, 278-279.
3. Díaz-Ortiz, A.; de la Hoz, A.; Langa, F. Microwave irradiation in solvent-free conditions: an eco-friendly methodology to prepare indazoles, pyrazolopyridines and bipyrazoles by cycloaddition reactions. Green Chem. 2000, 2, 165-172.
4. Shaabani, A.; Soleimani, E.; Khavasi, H. R.; Hoffmann, R.-D.; Rodewald, U. C.; Pottgen, R. An isocyanide-based three-component reaction: Synthesis of fully substituted N-alkyl-2-triphenylphosphoranylidene glutarimides. Tetrahedron Lett. 2006, 47, 5493-5496.
5. Keglevich, G.; Forintos, H.; Körtvélyesi, T. Synthesis and reactions of β-keto phosphoranes/ylides with cyclic or acyclic P-moiety. Curr. Org. Chem. 2004, 8, 1245-1261.
6. Ramazani, A.; Kazemizadeh, A. R.; Ahmadi, E.; Noshiranzadeh, N.; Souldozi, A. Synthesis and reactions of stabilized phosphorus ylides. Curr. Org. Chem. 2008, 12, 59-82.
7. Keglevich, G. [4 + 2] versus [2 + 2] cycloaddition's in the sphere of P-heterocycles as useful synthetic tools. Curr. Org. Chem. 2002, 6, 891-912.
8. Sahoo, M. K. Dimethyl acetylenedicarboxylate. Synlett. 2007, 2142-2143.
9. Alizadeh, A.; Rostamnia, S.; Zhu, L.-G. Reaction between tert-butyl isocyanide, dialkyl acetylenedicarboxylates, and aromatic carboxylic acids: an efficient method for the synthesis of dialkyl (E)-2-{[benzoyl(tert-butyl) amino]carbonyl}-2-butenedioate derivatives. Tetrahedron 2006, 62, 5641-5644.
10. Shaabani, A.; Soleimani, E.; Maleki, A. Ionic liquid promoted one-pot synthesis of 3-aminoimidazo[1,2-a]pyridines. Tetrahedron Lett. 2006, 47, 3031-3034.
11. Shaabani, A.; Teimouri, M. B.; Bijanzadeh, H. R. One-pot three component condensation reaction in water: an efficient and improved procedure for the synthesis of furo[2,3-d]pyrimidine-2,4(1H,3H)-diones. Tetrahedron Lett. 2002, 43, 9151-9154.
12. Shaabani, A.; Yavari, I.; Teimouri, M. B.; Bazgir, A.; Bijanzadeh, H. R. New and efficient synthesis of dialkyl 2-[1-p-nitrophenyl-2-(alkylamino)- 2-oxoethyl]malonates. Tetrahedron 2001, 57, 375-1378.
13. Ramazani, A.; Bodaghi, A. One-pot, four-component synthesis of dialkyl [indane-1,3-dione-2-ylidene]alkoxysuccinates. Tetrahedron Lett. 2000, 41, 567-568.
14. Ramazani, A.; Ahmadi, E. Manganese dioxide is an efficient catalyst for the stereoselective conversion of dialkyl 2-(imido-N-yl)-3- (triphenylphosphoranylidene) butanedioates to electron-poor (Z)-N-vinylimides in solvent-free conditions. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 2659-2661.
15. Multicomponent Reactions, J.; Zhu, H.; Bienayme, H. (Eds.); Wiley-VCH: Weinheim, 2005.
16. Ramazani, A.; Souldozi, A. Silica gel catalyzed conversion of dimethyl 2-(5-bromo-2-hydroxyphenyl)-3-(triphenylphosphoranylidene)butanedioate to methyl 6-bromo-2-oxo-2H-chromene-4-carboxylate in solvent-free conditions. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 2663-2666.
17. Ramazani, A.; Souldozi, A. Micrwave induced synthesis of coumarins from in situ generated stabilized phosphorus ylides in the presence of silica gel powder in solvent-free condition. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 529-533.
18. Ramazani, A.; Abbasi-Motejadded, A.; Ahmadi, E. Microwave-induced stereoselective conversion of dialkyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2- benzisothiazol-2-yl)-3-(triphenylphosphoranylidene)succinates to dialkyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)-2-butendioates in the presence of silica-gel powder in solvent-free conditions. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 233-236.
19. Noshiranzadeh, N.; Ramazani, A. Reaction between ortho-hydroxy aromatic aldehydes and dialkyl acetylenedicarboxylates in the presence of silica gel in solvent-free conditions: an efficient method for the synthesis of electron-poor aryl vinyl ethers and chromenes. Synth. Commun. 2007, 37, 3181-3189.
20. Noshiranzadeh, N.; Ramazani, A. The reaction of phenylhydrazine with sterically congested stabilized phosphorus ylides in the presence of silica gel powder in solvent-free conditions: A novel synthesis of fully substituted pyrazole derivatives. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 1109-1115.
21. Ghosh, S. K.; Hsung, R. P.; Liu, J. An anomeric control on remote stereochemistry in the synthesis of spiroketals. J. Am. Chem. Soc. 2005, 127, 8260-8261.