Marsicano Vincenzo, Arcadi Antonio, Chiarini Marco, Fabrizi Giancarlo, Goggiamani Antonella, Iazzetti Antonia
Dipartimento di Scienze Fisiche e Chimiche, Università di L'Aquila, Via Vetoio- 67010 Coppito (AQ), Italy.
Facoltà di Bioscienze e Tecnologie Agro-alimentari e Ambientali, Università di Teramo, Via R. Balzarini 1, 64100 - Teramo (Te), Italy.
Org Biomol Chem. 2021 Jun 16;19(23):5177-5190. doi: 10.1039/d1ob00795e.
A divergent domino condensation/biannulation reaction of β-(2-aminophenyl) α,β-ynones with 1,3-dicarbonyls to construct a polycyclic 4H-pyrano[3,4-c]quinoline core has been developed. The p-TsOH·H2O catalyzed reaction of β-(2-aminophenyl) α,β-ynones with β-ketoesters in ethanol proceeds with good to excellent yields to provide a simple and effective method for the synthesis of functionalized 4H-pyrano[3,4-c]quinolinones. Further elaboration of these latter derivatives with an excess of 20% NH4OH in EtOH at 50 °C helps achieve the synthesis of the perlodinine analogues benzo[c][2,7]naphthyridin-4(3H)-one derivatives in high yields. Moreover, the p-TsOH·H2O mediated reaction of β-(2-aminophenyl) α,β-ynones with β-di-ketones leads to the formation of a variety of structurally diverse 4H-pyrano[3,4-c]quinoline polycyclic ketals by the incorporation of an alcohol solvent molecule in a cascade fashion.
已开发出一种β-(2-氨基苯基)α,β-炔酮与1,3-二羰基化合物的发散性多米诺缩合/双环化反应，用于构建多环4H-吡喃并[3,4-c]喹啉核心。对甲苯磺酸一水合物催化β-(2-氨基苯基)α,β-炔酮与β-酮酯在乙醇中的反应，产率良好至优异，为合成官能化的4H-吡喃并[3,4-c]喹啉酮提供了一种简单有效的方法。在50℃下，用过量20%的氢氧化铵在乙醇中对这些后一种衍生物进行进一步处理，有助于高产率地合成过氯定类似物苯并[c][2,7]萘啶-4(3H)-酮衍生物。此外，对甲苯磺酸一水合物介导的β-(2-氨基苯基)α,β-炔酮与β-二酮的反应，通过以级联方式引入醇溶剂分子，导致形成各种结构多样的4H-吡喃并[3,4-c]喹啉多环缩酮。
