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제109회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Rh-catalyzed acylation and intramolecular cyclization of benzamides and aldehydes: synthesis of 3-hydroxyisoindolin-1-ones

2012년 2월 23일 15시 16분 10초
ORGN.P-951 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
4월 25일 (수요일) 18:00~21:00
저자 및
경희대학교 약학과, Korea
3-Hydroxyisoindolin-1-one is an important core structure of numerous natural products and artificially synthesized bioactive molecules, such as chilenine, a natural isoindolobenzazepine alkaloid isolated from Berberis empetrifolia, and fumadensine, an isoquinoline from Fumaria densiflora. Additionally, 3-hydroxyisoindolin-1-one moieties have been found in other bioactive molecules such as a Raf kinase inhibitor, an MEK protein kinase inhibitor as well as an HIV integrase inhibitor. 3-Hydroxyisoindolin-1-ones are also useful precursors for synthesis of arylmethyleneisoindolin-1-one compounds, which are important privileged structures of many biological active molecules. In addition, the products of dehydration of 3-hydroxyisoindolin-1-ones have been found to be useful intermediates in the total synthesis of isoindolobenzazepine alkaloids such as lennoxamine. Transition metal-catalyzed direct transformation of inactive C?H bonds has emerged as a powerful tool for the facile production of structurally diverse organic molecules. Since the pioneering efforts of Murai, great progress has been made in transition metal-catalyzed C?H bond functionalization upon trapping with appropriate electrophiles or nucleophiles under oxidative or basic conditions, respectively. In particular, reactions involving the activation of C?H bonds by neighboring directing group have been extensively investigated. As results, the combination of transition metals and directing groups provides efficient conversion of C?H bonds to C?C, C?X, C?O, and C?N bonds. Although carbon?carbon bond formation reactions using unsaturated C=C or C≡C bonds as the coupling partners have been well established, the reactions of C?H bonds and C-heteroatom unsaturated bonds, (e.g., C=O and C=N bonds), remain relatively unexplored. Herein we describe a rhodium-catalyzed oxidative acylation and intramolecular cyclization of primary benzamides with aryl aldehydes via direct sp2 C?H bond cleavage. In the presence of [Cp*RhCl2]2, AgSbF6, and silver carbonate as an oxidant, primary benzamides can be effectively carbonylated to 3-Hydroxyisoindolin-1-ones in good to high yields.