铁(III)促进(α-氨基)芳基乙酸中苄基 C-H 键的氧化环化以合成 4-芳基吡咯并[1,2-a]喹喔啉类化合物

Tuan H Ho
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引用次数: 0

摘要

利用氨基酸合成杂环化合物是一个前景广阔的合成领域。然而,开发将氨基酸转化为杂环的实用方法仍具有挑战性。鉴于α-氨基酸资源丰富或易于制备,我们在此报告一种用 1-(2-硝基芳基)吡咯环化 2-苯基甘氨酸衍生物中的苄基 C-H 键的方法。在乙酰丙酮酸铁(III)催化剂和碳酸钾碱存在下,反应进行顺利。研究了吡咯并[1,2-a]喹喔啉的范围。无论取代基的电子特性如何,都成功地分离出了吡咯并[1,2-a]喹喔啉去铆剂,产率从 42% 到 52% 不等。在 C4 位被杂环取代的吡咯并[1,2-a]喹喔啉,如吡啶和噻吩,是合格的底物。反应机理是以 2-苯基甘氨酸的脱羧/脱氨基顺序为起点,生成苯甲醛。据推测,铁催化剂可促进 1-(2-硝基芳基)吡咯的再还原,生成相应的苯胺。亚胺缩合后再进行环化和氧化,就能得到吡咯并[1,2-a]喹喔啉。我们的方法为将丰富的α-氨基酸转化为对合成有用的杂环提供了一种便捷的手段。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Iron(III) promoted oxidative annulation of benzylic C-H bonds in (α-amino)arylacetic acids for synthesis of 4-aryl pyrrolo[1,2-a]quinoxalines
Using amino acids for synthesis of heterocycles is a synthetically promising field. However, developing the practical methods for transformations of amino acids into heterocycles is still challenging. Given that alpha amino acids are abundant or easily prepared, herein we report a method for annulation of benzylic C-H bonds in derivatives of 2-phenylglycine with 1-(2-nitroaryl)pyrroles. The reactions proceeded well in the presence of iron(III) acetylacetonate catalyst and potassium carbonate base. Scope of pyrrolo[1,2-a]quinoxalines was studied. Regardless of electronic properties of substituents, the pyrrolo[1,2-a]quinoxaline de-rivatives were successfully isolated, as yields varied from 42% to 52%. Pyrrolo[1,2-a]quinoxalines substituted with heterocycles at C4 positions as pyridine and thiophene were competent substrates. Reaction mechanism was proposed to start with a decar-boxylative/deaminative sequence of 2-phenylglycine to afford benzaldehyde. The iron catalyst was presumed to facilitate the re-duction of 1-(2-nitroaryl)pyrroles to furnish the corresponding aniline. Imine condensation followed by cyclisation and oxidation would yield the pyrrolo[1,2-a]quinoxaline. Our method would offer a convenient tactic to transform abundant alpha amino acids into synthetically useful heterocycles.
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