Selective synthesis of heterocyclic compounds by the reactions of unsaturated ketones  Page description

Help  Print 
Back »
 

Details of project

  
Identifier
49468
Type K
Principal investigator Lévai, Albert
Title in Hungarian Heterociklusos vegyületek szelektív szintézise telítetlen ketonok reakcióival
Title in English Selective synthesis of heterocyclic compounds by the reactions of unsaturated ketones
Panel Chemistry 2
Department or equivalent Department of Organic Chemistry (University of Debrecen)
Participants Jekö, József
Starting date 2005-01-01
Closing date 2008-12-31
Funding (in million HUF) 7.020
FTE (full time equivalent) 2.88
state closed project





 

Final report

  
Results in Hungarian
Kalkonok, (3-kumarinil)-kalkonok, valamint dehidroecetsavból nyert telítetlen ketonok és hidrazinok reakciójával új 2-pirazolinokat szintertizáltunk. E vizsgálatok körében kiemelendők a (karboxi-fenil)-hidrazinok és ezen telítetlen ketonok erekakciónak vizsgálatai és karboxilcsoportot tartalmazó 2-pirazolinok szintézise. Izoflavonok, homoizoflavonok és 4-tioanalogonjaik és hidrazinok reakciójával új pirazolokat szintetizáltunk, amelyek tautoméria viszonyait NMR-spektroszkópiai mérésekkel és kvantumkémiai számításokkal tanulmányoztuk. Racionális eljárást dolgoztunk ki új, exociklusos (E,E)-cinnamilidén-ketonok előállítására. E vegyületeket kiindulási anyagokként használtuk eddig ismeretlen sztiril-pirazolinok és tetraciklusos sztiril-1,5-benzotiazepinek előáálítására. Résztesen tanulmányztuk ezen telítetlen ketonok dimetildioxiránnal történő epoxidálását és az így nyert epoxidik sztereokémiáját.
Results in English
New 2-pyrazolines have been synthesized by the reaction of chalcones, (3-coumarinyl)-chalcones and unsaturated ketones derived from dehydroacetic acid with hydrazines. Reactions of these unsaturated ketones with (carboxyphenyl)hydrazines for the preapartion of hitherto unknown (carboxyphenyl)-2-pyrazolines should be emphesized. New types of pyrazoles have been prepared by the reaction of isoflavones, homoisoflavones and their 4-thio analogues with hydrazines. Tautomerism of these new substances have been elucidated by NMR spectrsocopy and quantumchemical calculations. Versatile procedures were worked out for the synthesis of new exocyclic (E,E)-cinnamylideneketones. These substances were utilized as starting materials for the synthesis of hitherto unknown styrylpyrazolines and tetracyclic styryl-1,5-benzothiazepines. Epoxidation of these (E,E)-cinnamylideneketones with dimethyldioxirane has been achieved.
Full text http://real.mtak.hu/1980/
Decision
Yes





 

List of publications

  
H. Engi, N. Gyémánt, T. Lóránd, A. Lévai, I. Ocsovszki, J. Molnár: Cinnamylidene ketones as potential modulators of multidrug resistance in mause lymphoma and human cancer cell liens, In Vivo, 20, 119-124, 2006
A. Lévai, J. Jekő: Synthesis of 1,5-disubstituted 3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-pyrazolines, Monatsh. Chem., 137, 339-345, 2006
A. Lévai, J. Jekő:: Synthesis of carboxylic acid derivatives of 2-pyrazolines, Arkivoc 134-145 (2007(I)), 2007
A. Lévai, J. Jekő: Synthesis of 1-substituted 3,5-diaryl-2-pyrazolines by the reaction of alpha,beta-unsaturated ketones with hydrazines, J. Heterocyclic Chem. 43, 111-115, 2006
A. Lévai, J. Jekő, T. Gondos, A. Simon, G. Tóth:: Synthesis of benzo[b][1,4]thiazepines by the reaction of 3-aryl-1-(3-coumarinyl)propen-1-ones with 2-aminothiophenol, J. Heterocycl. Chem., 44, 1453-1458 (2007), 2007
A. Lévai, K. E. Kövér, J. Jekő:: Synthesis of tricyclic fused pyrazolines by the reaction of 3-arylidenechromanones and 3-arylidene-1-thiochromanones with hydrazine, Arkivoc 26-39 (2007(VIII), 2007
A. Lévai:: Synthesis of chlorinated 3,5-diaryl-2-pyrazolines by the reaction of chlorochalcones with hydrazines, Arkivoc 344-3352 (2005(IX), 2005
A. Lévai:: Synthesis of chlorinated 3,5-diaryl-2-pyrazolines by the reaction of chlorochalcones with hydrazines, Arkivoc 344-352 (2005(IX), 2005
A. Lévai: Synthesis and chemical transformations of benzoxazepines, Heterocycles 75, 2155-2185, 2008
A. Lévai, A. Kiss-Szikszai: Synthesis of optically active 1,5-benzothiazepines, Arkivoc 2008(I), 65-86, 2008
A. Lévai, J. Jekő: Synthesis of tetracyclic 1,5-benzothiazepines by the reaction of alpha,beta,gamma,delta-unsaturated ketones with 2-aminothiophenol, Arkivoc 2008(XVII), 234-240, 2008
A. Lévai, J. Jekő: Synthesis of 5-aryl-1-carboxyphenyl-3-(3-coumarinyl)-2-pyrazolines, Arkivoc 63-70 (2009(VI), 2009
A. Lévai, J. Jekő: A simple and efficient procedure for the stereoselective synthesis of trans-2,3,3a,4-tetrahydro-3-aryl-2-(4-carboxyphenyl)[1]benzopyrano[4,3-c]pyrazoles and their benzothiopyrano analogues, Acta Chim. Slov., megjelenés alatt, 2009
A. Lévai, A. Simon, A. Jenei, J. Jekő, G. Tóth: Synthesis of spiro-1-pyrazolines by the reaction of exocyclic alpha,beta,gamma,delta-unsaturated ketones with diazomethane, Monatsh. Chem, közlésre megküldve, 2009
A. Lévai, J. Jekő, D. I. Brahmbhatt: Synthesis of 1-substituted 5-aryl-3-(3-coumarinyl)-2-pyrazolines by the reaction of 3-aryl-(3-coumarinyl)propen-1-ones with hydrazines, J. Heterocyclic Chem. 42, 1231-1235, 2005
S. Kéki, L. Nagy, Gy. Deák, A. Lévai, M. Zsuga: Matrix-assisted laser desorption/ionization and electronspray ionization mass spectrometric study of 2,3-dihydro-1,4-benzoxazepines, Rapic Comm. Mass Spectrom., 19, 1263-1267 (2005), 2005
A. Lévai, A. M. S. Silva, J. A. S. Cavaleiro, I. Alkorta, J. Elguero, J. Jekő: Synthesis of pyrazoles by treatment of 3-benzylchromones, 3-benzylflavones and their 4-thio analogues with hydrazine, Eur. J. Org. Chem. 2825-2832, 2006
A. Lévai, G. Tóth, T. Gondos, J. Jekő, D. I. Brahmbhatt:: Reductive formation of 1,5-benzothiazepines, Heterocycles, 68, 1319-1324, 2006
A. Lévai, J. Jekő: Synthesis of 1-substituted 5-aryl-3-styryl-2-pyrazolines and 3-aryl-5-styryl-2-pyrazolines by the reaction of dibenzylideneacetones and E,E-cinnamylideneacetophenones wit, J. Heterocyclic Chem., 43, 1303-1309, 2006
G. Tóth, A. Simon, T. Gondos, A. Lévai, J. Jekő, F. Andrási: NMR spectroscopic structure elucidation of the products of the reaction of 3-(3-aryl-3-oxopropenyl)-chromen-4-ones with 1,2-phenylenediamine, Magn. Rson Chem. 44, 656-860, 2006
A. Lévai, A. M. S. Silva, J. A. S. Cavaleiro, J. Elguero, I. Alkorta, J. Jekő:: Synthesis of 4-aryl-3(5)-(2-hydroxyphenyl)pyrazoles by the reaction of isoflavones and their 4-thio analogues with hydrazine derivatives, Aust. J. Chem, in press, 2007
S. Kéki, L. Nagy, J. Török, K. Tóth, A. Lévai, M. Zsuga:: Energy-variable collision-induced dissociation study of 1,3,5-trisubstituted 2-pyrazolines by electronspray mass spectrometry, Rapid Commun. Mass Spectrom., 21, 1799-1808 (2007), 2007
G. Tóth, A. Simon, A. Jenei, J. Jekő, A. Lévai: NMR spectroscopic elucidation of the structure and stereochemistry of tricyclic 3-styrylpyrazolines, Magn. Reson. Chem. 46, 1025-1029, 2008
A. Lévai, A. M. S. Silva, C. M. M. Santos, J. A. S. Cavaleiro, J. Jekő: Dimethyldioxirane oxidation of exocyclic (E,E)-cinnamylideneketones, Aust. J. Chem. 62, 82-89, 2009



Back »