Acid-catalyzed domino reaction of 2-(2-methoxyphenyl)-substituted cycloalkanols with aromatic/heteroaromatic ortho-aminonitriles: Diastereoselective access to polycyclic acridines and related heterocycles

IF 1.4 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-11-19 DOI:10.1016/j.tetlet.2025.155904

Yuliya S. Rozhkova, Arina S. Pegushina, Vyacheslav V. Morozov, Daria V. Eroshenko, Yurii V. Shklyaev

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Abstract

A novel acid-catalyzed domino reaction of 2-(2-methoxyphenyl)-substituted cycloalkanols with aromatic and heteroaromatic ortho-aminonitriles was developed, resulting in the diastereoselective formation of new polycyclic acridines and related heterocycles, including partially hydrogenated quinolino[4,3,2-kl]acridines, cyclopenta[5,6]pyrido[4,3,2-kl]acridine, and fused pyrido[4,3,2-gh]phenanthridines, in 14–81 % yields. The developed domino sequence involves initial dearomative electrophilic ortho-spirocyclization via the Ritter reaction, followed by intramolecular nucleophilic trapping of the spiro-σ-intermediate by the amino group and subsequent aromatization via [1,2]-alkyl shift. Several of the synthesized quinolino[4,3,2-kl]acridines showed high antibacterial activity against S. epidermidis ATCC 29887 and M. smegmatis mc² 155.

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2-（2-甲氧基苯基）取代环烷醇与芳香/杂芳香邻氨基腈的酸催化多米诺反应：多环吖啶和相关杂环的非对映选择性获取

研究了2-（2-甲氧基苯基）取代环烷醇与芳香族和杂芳香族邻氨基腈的酸催化多米诺反应，得到了新的多环吖啶和相关的杂环化合物，包括部分氢化喹啉[4,3,2-kl]吖啶、环五[5,6]吡啶[4,3,2-kl]吖啶和融合吡啶[4,3,2-gh]菲啶，产率为14 - 81%。发展的多米诺骨牌序列包括通过Ritter反应进行的初始脱芳亲电邻螺旋环化，随后氨基对螺旋-σ-中间体进行分子内亲核俘获，随后通过[1,2]-烷基移位进行芳构化。合成的几种喹诺啉[4,3,2-kl]吖啶类化合物对表皮葡萄球菌ATCC 29887和耻垢分枝杆菌mc2155具有较高的抑菌活性。

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.