7 research outputs found
[1,5]-Hydride Shift-Cyclization versus C(sp2)-H Functionalization in the Knoevenagel-Cyclization Domino Reactions of 1,4- and 1,5-Benzoxazepines
Domino cyclization reactions of N-aryl-1,4- and 1,5-benzoxazepine derivatives involving [1,5]-hydride shift or C(sp2)-H functionalization were investigated. Neuroprotective and acetylcholinesterase activities of the products were studied. Domino Knoevenagel-[1,5]-hydride shift-cyclization reaction of N-aryl-1,4-benzoxazepine derivatives with 1,3-dicarbonyl reagents having active methylene group afforded the 1,2,8,9-tetrahydro-7bH-quinolino [1,2-d][1,4]benzoxazepine scaffold with different substitution pattern. The C(sp3)-H activation step of the tertiary amine moiety occurred with complete regioselectivity and the 6-endo cyclization took place in a complete diastereoselective manner. In two cases, the enantiomers of the chiral condensed new 1,4-benzoxazepine systems were separated by chiral HPLC, HPLC-ECD spectra were recorded, and absolute configurations were determined by time-dependent density functional theory- electronic circular dichroism (TDDFT-ECD) calculations. In contrast, the analogue reaction of the regioisomeric N-aryl-1,5-benzoxazepine derivative did not follow the above mechanism but instead the Knoevenagel intermediate reacted in an SEAr reaction [C(sp2)-H functionalization] resulting in a condensed acridane derivative. The AChE inhibitory assays of the new derivatives revealed that the acridane derivative
had a 6.98 uM IC50 value
Substantial expression of luteinizing hormone-releasing hormone (LHRH) receptor type I in human uveal melanoma
Kondenzált benzoxazepin származĂ©kok előállĂtása domino Knoevenagel-tercier-amino effektus gyűrűzárási reakciĂłkkal
Domino Gyűrűzárási ReakciĂłk Vizsgálata Kondenzált Királis O-heterociklusok ElőállĂtására
A diplomamunkám keretĂ©ben cĂ©lul tűztĂĽk ki o-formil-arilĂ©ter szerkezeti egysĂ©get tartalmazĂł származĂ©kok előállĂtását 3-formilkromon Ă©s fahĂ©jalkohol kiindulási anyagokbĂłl, Ă©s átalakĂtásukat aktĂv metilĂ©n csoportot tartalmazĂł bĂ©ta-dikarbonil reagensekkel domino Knoevenagel-hetero Diels Alder gyűrűzárási reakciĂłkban.MSc/MAVegyĂ©s
Naftil-1,4-benzoxazepin származékok domino gyűrűzárási reakciói
KĂsĂ©rleteink során sikerĂĽlt megvalĂłsĂtani 2-hidroxi-acetofenonbĂłl, Ă©s 1- illetve 2-naftalĂ©n aldehidbĹ‘l kiindulva a megfelelĹ‘en szubsztituált kalkonok előállĂtását, majd ezek flavanonná törtĂ©nĹ‘ gyűrűzárását. A flavanonok származĂ©kokbĂłl kiindulva sikeresen hajtottunk vĂ©gre gyűrűbĹ‘vĂtĂ©si reakciĂłkat, majd a kapott laktámokat lĂtium-alumĂnium hidrid/THF (LAH/THF) szuszpenziĂł segĂtsĂ©gĂ©vel redukáltuk. Az SNAr reakciĂłt 2-klĂłr-5-nitrobenzaldehiddal valĂłsĂtottuk meg jĂł kitermelĂ©ssel. Az Ăgy előállĂtott származĂ©kokbĂłl kĂĽlönbözĹ‘ aktĂv metilĂ©n csoportot tartalmazĂł reagensekkel domino Knoevenagel-Reinhoudt reakciĂłkat hajtottunk vĂ©gre, potenciálisan idegsejtvĂ©dĹ‘ vegyĂĽletek előállĂtása cĂ©ljábĂłl. A reakciĂłkat 1,3-dimetilbarbitursavval, meldrumsavval elvĂ©gezve gyűrűzárt termĂ©keket, 1,3-indándion esetĂ©n vinil termĂ©keket kaptunk. Malononitril, illetve benzoilacetonitril alkalmazása során az 1H NMR mĂ©rĂ©sek alapján vinil termĂ©k:gyűrűzárt termĂ©k 3:1 arányĂş keverĂ©ke kĂ©pzĹ‘dött.BSc/BABiomĂ©rnökL