Electrophilic amination reactions with 1H‐indazole‐3‐carboxylates: Synthesis of amino acid frameworks and 3‐amino‐2‐oxindoles,Journal of Heterocyclic Chemistry

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Electrophilic amination reactions with 1H‐indazole‐3‐carboxylates: Synthesis of amino acid frameworks and 3‐amino‐2‐oxindoles
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-05-14 , DOI: 10.1002/jhet.4015
Isao Mizota ₁ , Mayuko Mori ₁ , Makoto Shimizu _{1,

2}

Affiliation

Reaction of 1‐ sulfonylindazole‐3‐carboxylates with various Grignard reagents effects the N ‐N bond cleavage of the hydrazone moiety with the first nucleophile and the subsequent N ‐alkylation gives N ,N ‐dialkylation products in good yields. A new strategy for the synthesis of α‐(2‐arylsulfonamide)phenylglycine, a precursor to tissue factor/factor VIIa inhibitors is also described. Moreover, the synthesis of quaternary 3‐aminooxindoles is developed, utilizing this N ,N ‐dialkylation reaction, followed by intramolecular cyclization/nucleophilic addition reaction.

中文翻译：

与1H-吲唑-3-羧酸盐的亲电胺化反应：氨基酸骨架和3-氨基-2-氧吲哚的合成

的1反应- sulfonylindazole -3-羧酸与各种格氏试剂效果Ñ - Ñ与所述第一亲核试剂腙部分的键裂解和随后的Ñ烷基化给出Ñ，Ñ -dialkylation制品以良好的收率。还描述了一种合成α-（2-芳基磺酰胺）苯基甘氨酸的新策略，α-（2-芳基磺酰胺）苯基甘氨酸是组织因子/因子VIIa抑制剂的前体。此外，利用该N，N-二烷基化反应，然后进行分子内环化/亲核加成反应，开发了季3-氨基羟吲哚的合成方法。

更新日期：2020-07-15

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