A novel intramolecular Ugi reaction with 7-azabicyclo[2.2.1]heptane derivatives followed by post-condensation acylations: a new entry to azanorbornyl peptidomimetics

Andrea Basso; Luca Banfi; Giuseppe Guanti; Renata Riva

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A novel intramolecular Ugi reaction with 7-azabicyclo[2.2.1]heptane derivatives followed by post-condensation acylations: a new entry to azanorbornyl peptidomimetics

机译：新型分子内Ugi反应与7-氮杂双环[2.2.1]庚烷衍生物，然后缩合后酰化：氮杂降冰片肽模拟物的新进入

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β-Amino acids have been employed in the past as bifunctional building blocks in intramolecular Ugi multicomponent reactions to yield β-lactam derivatives. By using 7-azabicyclo[2.2.1]heptane-2-carboxylic acid, a different outcome has been observed and rationalised. The final compounds are polyfunctionalised azabicyclic peptidomimetics, and further elaboration can be achieved exploiting an additional carboxylic group that is not involved in the multicomponent step.

机译：过去，β-氨基酸已在分子内Ugi多组分反应中用作双功能结构单元，从而生成β-内酰胺衍生物。通过使用7-氮杂双环[2.2.1]庚烷-2-羧酸，观察到了不同的结果并得到了合理化。最终化合物是多官能化的双氮杂双环拟肽，并且可以利用多组分步骤中不涉及的其他羧基实现进一步的加工。

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《Organic & biomolecular chemistry》 |2009年第1期|253-258|共6页
作者
Andrea Basso; Luca Banfi; Giuseppe Guanti; Renata Riva;
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Universita degli Studi di Genova, Dipartimenlo di Chimica e Chimica Industriale, Via Dodecaneso 31, 16146, Genova, Italy;

Universita degli Studi di Genova, Dipartimenlo di Chimica e Chimica Industriale, Via Dodecaneso 31, 16146, Genova, Italy;

Universita degli Studi di Genova, Dipartimenlo di Chimica e Chimica Industriale, Via Dodecaneso 31, 16146, Genova, Italy;

Universita degli Studi di Genova, Dipartimenlo di Chimica e Chimica Industriale, Via Dodecaneso 31, 16146, Genova, Italy;

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1. Mechanistic Analysis of Intramolecular Free Radical Reactions toward Synthesis of 7-Azabicyclo[2.2.1]heptane Derivatives [J] . Elena Soriano, Jose′ Marco-Contelles The Journal of Organic Chemistry . 2009,第11期

机译：分子内自由基反应对7-氮杂双环[2.2.1]庚烷衍生物合成的机理分析
2. Chemistry of 7-Azabicyclo[2.2.1]hepta-2,5-dienes, 7-Azabicyclo[2.2.1]hept-2-enes, and 7-Azabicyclo[2.2.1]heptanes [J] . Zhengming Chen, Mark L. Trudell Chemical Reviews . 1996,第3期

机译：7-氮杂双环[2.2.1]庚-2,5-二烯，7-氮杂双环[2.2.1]庚-2-烯和7-氮杂双环[2.2.1]庚烷的化学
3. A Straightforward Entry to 7-Azabicyclo[2.2.1]heptane-1-carbonitriles in the Synthesis of Novel Epibatidine Analogues [J] . Heugebaert T, Van Hevele J, Couck W, European journal of organic chemistry . 2010,第6期

机译：直接合成新型Epibatidine类似物的7-氮杂双环[2.2.1]庚烷-1-腈
4. 7-Azabicyclo2.2.1heptane-2-carboxylic acids as peptidomimetic conformational constraints. NK2 antagonists as an example [C] . Susan Northfield, Michelle Camerino, Hayley Mulvey International Peptide Symposium . 2009

机译：7-氮杂双环2.2.1庚烷-2-羧酸作为肽模拟构象约束。 NK2拮抗剂作为一个例子
5. I. The tandem chain extension-acylation reaction. II. Synthesis of papyracillic acid A: Application of the tandem homologation-acylation reaction. III. Synthesis of tetrahydrofuran-based peptidomimetics. [D] . Spencer, Carley Meredith. 2013

机译：I.串联链延伸-酰化反应。二。纸莎草酸A的合成：串联同源化-酰化反应的应用。三，合成基于四氢呋喃的拟肽。
6. Synthesis of acylhydrazino-peptomers a new class of peptidomimetics by consecutive Ugi and hydrazino-Ugi reactions [O] . Angélica de Fátima S Barreto, Veronica Alves dos Santos, Carlos Kleber Z Andrade 2016

机译：通过连续的Ugi和肼基-Ugi反应合成一类新型的拟肽酰基肼基-肽
7. Synthesis of new 7-azabicyclo[2.2.1]heptane derivatives [O] . José Marco-Contelles, Elena Soriano, Elena Gómez-Sánchez, 2009

机译：新的7-氮杂双环[2.2.1]庚烷衍生物的合成
8. Importance of the Structure of the Phosphorus Functionality in Allowing Dihedral Angle Control of Vicinal 13C-31P Coupling. Carbon-13 NMR Spectra of 7-Substituted Bicyclo(2.2.1)Heptane Derivatives. [R] . Quin, L. D., Littlefield, L. B. 1978

机译：作者：张莹莹，王玮，王莹，工业用水与废水INDUsTRIaL WaTER＆WasTEWaTER侧位13C-31p耦合二面角控制中磷功能结构的重要性。 7-取代双环（2.2.1）庚烷衍生物的碳-13NmR谱。

A novel intramolecular Ugi reaction with 7-azabicyclo[2.2.1]heptane derivatives followed by post-condensation acylations: a new entry to azanorbornyl peptidomimetics

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