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Synthesis of 1,4-Diazepanes and Benzo[b][1,4]diazepines by a Domino Process Involving the In Situ Generation of an Aza-Nazarov Reagent.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-08-21 , DOI: 10.1021/acs.joc.0c01774 Swarupananda Maiti 1 , Marco Leonardi 1 , Ángel Cores 1 , Giammarco Tenti 1 , M Teresa Ramos 1 , Mercedes Villacampa 1 , J Carlos Menéndez 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-08-21 , DOI: 10.1021/acs.joc.0c01774 Swarupananda Maiti 1 , Marco Leonardi 1 , Ángel Cores 1 , Giammarco Tenti 1 , M Teresa Ramos 1 , Mercedes Villacampa 1 , J Carlos Menéndez 1
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A step- and atom-economical protocol allowing the synthesis of 1,4-diazepanes and also tetrahydro- and decahydro-1,5-benzodiazepines is described. The method proceeds from very simple starting materials such as 1,2-diamines and alkyl 3-oxohex-5-enoates and can be performed under solvent-free conditions in many instances. The key event of this process was the generation in situ of an aza-Nazarov reagent and its subsequent intramolecular aza-Michael cyclization. An intermolecular version of the reaction was also established and applied to the synthesis of the first example of the pyrrolo[1,2-a][1,5]diazonine framework.
中文翻译：
通过涉及就地生成Aza-Nazarov试剂的多米诺法合成1,4-二氮杂环庚烷和苯并[b] [1,4]二氮杂ze。
描述了一种步骤和原子经济的方案，其允许合成1,4-二氮杂庚烷以及四氢-和十氢-1,5-苯并二氮杂pine。该方法从非常简单的起始原料，例如1,2-二胺和3-氧杂己基-5-烯酸烷基酯出发，在许多情况下可以在无溶剂条件下进行。该过程的关键事件是aza-Nazarov试剂的原位生成及其随后的分子内aza-Michael环化。还建立了反应的分子间形式，并将其用于吡咯并[1,2- a ] [1,5]重氮骨架的第一个实例的合成。
更新日期：2020-09-20
中文翻译：
通过涉及就地生成Aza-Nazarov试剂的多米诺法合成1,4-二氮杂环庚烷和苯并[b] [1,4]二氮杂ze。
描述了一种步骤和原子经济的方案，其允许合成1,4-二氮杂庚烷以及四氢-和十氢-1,5-苯并二氮杂pine。该方法从非常简单的起始原料，例如1,2-二胺和3-氧杂己基-5-烯酸烷基酯出发，在许多情况下可以在无溶剂条件下进行。该过程的关键事件是aza-Nazarov试剂的原位生成及其随后的分子内aza-Michael环化。还建立了反应的分子间形式，并将其用于吡咯并[1,2- a ] [1,5]重氮骨架的第一个实例的合成。
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