Environmentally desirable synthesis: one-pot and solvent free formation of arylidenes compounds from gem-diacetates
Abstract
Abstract:Heterogeneous acid catalysts are of importance in the fine chemicals area, and several been investigated in reactions such as the Knoevenagel reaction, an important reaction with pronounced solvent dependency. The condensation of active methylene compounds with gem-diacetates in the presence of acid aluminosilicates (montmorillonite KSF, K10/ZnCl2) without solvent and under microwave irradiation, an efficient of synthesis of arylidenes compounds without isolation of aldehydes compounds. Cleavage of arylidene rhodanine derivative in position 5 in basic medium on Potassium Fluoride–Barium Oxide (BaO-KF) under focused microwave irradiation and free solvent is a simple and effective method for synthesis of, β-aryl-α-thiolacrylic acids.
Full Text:
PDFReferences
Brown, R.; Kelly, C.; Wiberly, S. E. The Production of 3-Benzylidene-6-isobutylidene-2,5-dioxopiperazine, 3,6- Dibenzylidene-2,5-dioxopiperazine, 3-Benzyl-6-benzylidene-2,5-dioxopiperazine, and 3,6-Dibenzyl-2,5-dioxopiperazine by a Variant of Streptomyces nourseil. J Org Chem 30(1965)277.
Rao, K. V.; Cullen, W. P. E-73 : An Antitumor Substance. Part I, Isolation and Characterization. J Am Chem Soc 82(1960)1127.
Fukushima, K.; Arai, T. Biological activities of albonoursin. J antibiotics 26(1973)175
Villemin, D.; Ben Alloum, A. Potassium Fluoride on Alumina: Condensation of 1,4-Diacetylpiperazine-2,5- Dione with Aldehydes. Dry Condensation Under Microwave Irradiation. Synthesis of Albonursin and Analogues. Synth Commun 20(1990)3325.
Singh, S. P.; Raman, K.; Styenberg, V. I.; Chemistry and biological activity of thiazolidinones. Chem Rev 81(1981)175
Bhargav, A. P.; Charles, R.; Ashby, J.r.; Diane, H., Tanaji T. The synthesis and SAR study of phenylalanine-derived (Z)-5-arylmethylidene rhodanines as anti-methicillin-resistant Staphylococcus aureus (MRSA) compounds. Bioorganic & Medicinal Chemistry Letters 23(2013) 5523–5527
Windholz (ed), The Merck Index, 10th edition, Merck & Co. Inc., Ratway, 1983; pp.1521.
Shukla, S. K.; Singh, S. P.; Awasthi. L. P.; Mukherjee, D. D. Indian J Pharm Sci 44(1982)153;Chem. Abtstr 99(1983)22365u.
Reginato, M. J.; Lazar, M. A.; Mechanisms by which Thiazolidinediones Enhance Insulin Action, TEM 10(1999)1.
Zhang,B. B.; Muller, D. E.; New approaches in the treatment of type 2 diabetes ; Current Opinion in Chemical Biology 4(2000)461.
Sing, W. T.; Lee, C. L.; Yeo, S. L.; Lim, S. P.; Sim, M. M,; Arylalkylidene Rhodanine with Bulky and Hydrophobic Functional Group as Selective HCV NS3 Protease Inhibitor. Biorg Med Chem Lett 11(2001)91.
Mustapha, A.; Asker, W.; Shalaby, A. F. A. Action of Grignard Reagents. XIV.l Action of Organomagnesium Compounds on 1-Phenyl-3-methyl-4-arylidene-5-pyrazolones. Their Behavior toward Aromatic Secondary Amines and Aromatic Thiols. J Am Chem Soc 81(1959)6007.
Mustafa, A.; Asker , W.; Harhash, A. H.; Fleifel, A. M.; Reactivity of unsaturated centers in heterocycles and chalcones towards diazoalkanes. Tetrahedron.21(1965)2215–2229.
Desimoni, G.; Astolfi, L.; Tacconi, G. heterodiene syntheses-xii’ the conformational analysis of cfs and trans 2-alkoxy-4-phenyl-2,3-dihydropyran[2,3-c] pyrazoles: steric interactions and the anomeric effect ; Tetrahedron, 29(1973)2627.
El-Sayed, A.; Fathy, A. A.; Momdouh, S. Synthesis of Some Pyrazolo [Diazepine, Pyrazole, Isoxazole and Pyrimidine] Derivatives and Related Compounds. Z. Naturforsch. 35b(1980)1313-1316.
Wheeler, H. L.; Jamieson, G. S. on sotie aldehyde condensation products of arylpseudothiohydantoins. ; J Am Chem Soc 25(1903)366. Croxall, W. J., Chien-pen, L.; Elwood, Y.; Shropshire, R. M. 3-TrichloromethanesuIfenyloxazolidine- and, Thiaxolidine-2,4diones. J Am Chem Soc 75(1953)5419.
Mustapha, A.; Asker, W.; Khattab, S.; Sobhy, M. E.; Fleifel, A. M. Action of Grignard Reagents. XV1I.l Action of Organomagnesium Compounds on 5-Arylidene Derivatives of 3-Arylrhodanines, of 3-p-Tolyl-2,4-thiazolidinedione and on 2-Arylidene-3 (2H)-4,5-benzthianaphthenone-l, 1-dioxides. J Am Chem Soc 82(1960)2029
E. Campaigne, R. E. Cline, Preparation and Absorption Spectra of Some p-Aryl-a-Mercaptoacrylic Acids and Related Disulfides, J Org Chem 21(1956)32.
Gengelman, L. Monatsh Chem 43(1922)537.Girard, M. L.; Dreux, C. Bull Soc Chim. Fr(1958)3461.
Reginato, M. J.; Lazar, M. A. Mechanisms by which Thiazolidinediones Enhance Insulin Action. TEM, 10(1999)1.
Zhang, C.X.; Lippard, S. J.; New Metal Complexes as Potential Therapeutics. Current Opinion in Chemical Biology, 7 4 (2003) 481-489.
Brown, F. C.; Bradsher, C. F.; Bond, S. M.; Potter, M. Rhodanine Derivatives, J Am Chem Soc., 73(1951)2357.
Refbacks
- There are currently no refbacks.