2-(Substituted amino)-8-azachromones from 4,6-Diaryl-2-pyridones: A Synthetic Strategy toward Compounds of Broad Structural Diversity.,The Journal of Organic Chemistry

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2-(Substituted amino)-8-azachromones from 4,6-Diaryl-2-pyridones: A Synthetic Strategy toward Compounds of Broad Structural Diversity.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-09-01 , DOI: 10.1021/acs.joc.0c01561
Steve Saulnier ₁ , Rayane Ghoteimi ₁ , Christophe Mathé ₁ , Suzanne Peyrottes ₁ , Jean-Pierre Uttaro ₁

Affiliation

3-Acetoacetyl-4,6-diaryl-2-pyridones are synthesized in three steps from chalcones and then condense with carbon disulfide to afford 8-azachromones containing a methylthio group at C2. This leaving group offers an entry point for the insertion of more complex moieties via nucleophilic substitution. For this purpose, N-nucleophiles are explored according to their positions in the Mayr’s nucleophilicity scale (N parameter), and three main classes are distinguished depending on whether the substitution takes place from their neutral forms, from their deprotonated anionic forms, or under nucleophilic catalysis. A broad range of primary and secondary amines may be inserted by this method, including enantiomerically pure amino acids, enabling us to explore structural diversity.

中文翻译：

来自4,6-二芳基-2-吡啶酮的2-（取代的氨基）-8-氮杂色酮：合成化合物的广泛结构多样性。

从查耳酮分三步合成3-乙酰乙酰基-4,6-二芳基-2-吡啶酮，然后与二硫化碳缩合，得到在C2处含有甲硫基的8-氮杂色酮。该离去基团提供了通过亲核取代插入更多复杂部分的切入点。为此，根据其在Mayr亲核标度中的位置（N参数）来探索N-亲核体，根据取代是从其中性形式，从去质子化的阴离子形式还是在亲核性下进行区分，分为三个主要类别催化。通过这种方法可以插入各种各样的伯胺和仲胺，包括对映体纯的氨基酸，使我们能够探索结构的多样性。

更新日期：2020-09-20

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