Direct α-Imination of N-Acyl Pyrazoles with Nitrosoarenes,Organic Letters

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Direct α-Imination of N-Acyl Pyrazoles with Nitrosoarenes
Organic Letters ( IF 4.9 ) Pub Date : 2019-06-21 00:00:00 , DOI: 10.1021/acs.orglett.9b01913
Chiara Volpe ₁ , Sara Meninno ₁ , Giulia Mirra ₁ , Jacob Overgaard ₂ , Amedeo Capobianco ₁ , Alessandra Lattanzi ₁

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Unprecedented α-imino N-acyl pyrazoles were efficiently and selectively prepared through the 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)-catalyzed reaction of nitrosoarenes with N-acyl pyrazoles via an N-nitroso aldol reaction/dehydration sequence. The α-imino acyl pyrazoles were demonstrated to be new versatile intermediates for practical one-pot syntheses of α-imino amides, dipeptide precursors, esters, and β-amino alcohols. The synthetic method competes with known protocols in terms of ready availability of the reagents and catalyst, mild and catalytic reaction conditions, gram-scale applicability, and scope of the α-imino acid derivatives achievable.

中文翻译：

N-酰基吡唑与亚硝基芳烃的直接α-氨基化

通过1,5,7-三氮杂双环[4.4.0]癸-5-烯（TBD）催化的亚硝基芳烃与N-酰基吡唑的反应，通过N-亚硝基，有效地，选择性地制备了前所未有的α-亚氨基N-酰基吡唑羟醛反应/脱水顺序。已证明α-亚氨基酰基吡唑是α-亚氨基酰胺，二肽前体，酯和β-氨基醇的一锅合成的新型通用中间体。在试剂和催化剂的容易获得，温和的和催化的反应条件，克规模的适用性以及可获得的α-亚氨基酸衍生物的范围方面，该合成方法与已知的方案竞争。

更新日期：2019-06-21

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