[1,5]-Hydride Shift-Cyclization versus C(sp2)-H Functionalization in the Knoevenagel-Cyclization Domino Reactions of 1,4- and 1,5-Benzoxazepines
  • Metaadatok
Tartalom: http://real.mtak.hu/114310/
Archívum: REAL
Gyűjtemény: Status = Published
Subject = Q Science / természettudomány: QD Chemistry / kémia: QD01 Analytical chemistry / analitikai kémia
Subject = Q Science / természettudomány: QD Chemistry / kémia: QD04 Organic chemistry / szerves kémia
Type = Article
Cím:
[1,5]-Hydride Shift-Cyclization versus C(sp2)-H Functionalization in the Knoevenagel-Cyclization Domino Reactions of 1,4- and 1,5-Benzoxazepines
Létrehozó:
Vargáné Szalóki, Dóra
Tóth, László
Buglyó, Balázs
Kiss-Szikszai, Attila
Mándi, Attila
Mátyus, Péter
Antus, Sándor
Chen, Yinghan
Li, Dehai
Tao, Lingxue
Zhang, Haiyan
Kurtán, Tibor
Kiadó:
MDPI
Dátum:
2020-03-11
Téma:
QD01 Analytical chemistry / analitikai kémia
QD04 Organic chemistry / szerves kémia
Tartalmi leírás:
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.
Nyelv:
angol
Típus:
Article
PeerReviewed
info:eu-repo/semantics/article
Formátum:
text
Azonosító:
Vargáné Szalóki, Dóra and Tóth, László and Buglyó, Balázs and Kiss-Szikszai, Attila and Mándi, Attila and Mátyus, Péter and Antus, Sándor and Chen, Yinghan and Li, Dehai and Tao, Lingxue and Zhang, Haiyan and Kurtán, Tibor (2020) [1,5]-Hydride Shift-Cyclization versus C(sp2)-H Functionalization in the Knoevenagel-Cyclization Domino Reactions of 1,4- and 1,5-Benzoxazepines. MOLECULES, 25. p. 1265. ISSN 1420-3049
Kapcsolat:
10.3390/molecules25061265