当前位置：
X-MOL 学术
›
Org. Biomol. Chem.
›
论文详情
Our official English website, www.x-mol.net, welcomes your
feedback! (Note: you will need to create a separate account there.)
C4-C5 fused pyrazol-3-amines: when the degree of unsaturation and electronic characteristics of the fused ring controls regioselectivity in Ullmann and acylation reactions.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-06-17 , DOI: 10.1039/d0ob00796j Elisabeth Bou-Petit 1 , Arnau Plans 1 , Nieves Rodríguez-Picazo 1 , Antoni Torres-Coll 1 , Cristina Puigjaner 2 , Mercè Font-Bardia 2 , Jordi Teixidó 1 , Santiago Ramon Y Cajal 3 , Roger Estrada-Tejedor 1 , José I Borrell 1
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-06-17 , DOI: 10.1039/d0ob00796j Elisabeth Bou-Petit 1 , Arnau Plans 1 , Nieves Rodríguez-Picazo 1 , Antoni Torres-Coll 1 , Cristina Puigjaner 2 , Mercè Font-Bardia 2 , Jordi Teixidó 1 , Santiago Ramon Y Cajal 3 , Roger Estrada-Tejedor 1 , José I Borrell 1
Affiliation
|
Pyrazol-3-amine is a scaffold present in a large number of compounds with a wide range of biological activities and, in many cases, the heterocycle is C4–C5 fused to a second ring. Among the different reactions used for the decoration of the pyrazole ring, Ullmann and acylation have been widely applied. However, there is some confusion in the literature regarding the regioselectivity of such reactions (substitution at N1 or N2 of the pyrazole ring) and no predictive rule has been so far established. As a part of our work on 3-amino-pyrazolo[3,4-b]pyridones 13, we have studied the regioselectivity of such reactions in different C4–C5 fused pyrazol-3-amines. As a rule of thumb, the Ullmann and acylation reactions take place, predominantly, at the NH and non-protonated nitrogen atom of the pyrazole ring respectively, of the most stable initial tautomer (1H- or 2H-pyrazole), which can be easily predicted by using DFT calculations.
中文翻译：
C4-C5稠合的吡唑-3-胺：当不饱和度和稠合环的电子特性控制Ullmann中的区域选择性和酰化反应时。
吡唑-3-胺是存在于许多具有广泛生物活性的化合物中的支架，在许多情况下，杂环是C4–C5与第二个环稠合。在用于装饰吡唑环的不同反应中，Ullmann和酰化已得到广泛应用。然而，关于此类反应的区域选择性（吡唑环的N1或N2取代）的文献存在混淆，并且迄今尚未建立预测规则。作为我们对3-氨基-吡唑并[3,4- b ]吡啶酮的研究13，我们研究了在不同的C4–C5稠合的吡唑-3-胺中此类反应的区域选择性。根据经验，Ullmann和酰化反应主要发生在最稳定的初始互变异构体（1H-或2H-吡唑）的吡唑环的NH和非质子化氮原子上。通过使用DFT计算进行预测。
更新日期：2020-07-15
中文翻译：
C4-C5稠合的吡唑-3-胺：当不饱和度和稠合环的电子特性控制Ullmann中的区域选择性和酰化反应时。
吡唑-3-胺是存在于许多具有广泛生物活性的化合物中的支架，在许多情况下，杂环是C4–C5与第二个环稠合。在用于装饰吡唑环的不同反应中，Ullmann和酰化已得到广泛应用。然而，关于此类反应的区域选择性（吡唑环的N1或N2取代）的文献存在混淆，并且迄今尚未建立预测规则。作为我们对3-氨基-吡唑并[3,4- b ]吡啶酮的研究13，我们研究了在不同的C4–C5稠合的吡唑-3-胺中此类反应的区域选择性。根据经验，Ullmann和酰化反应主要发生在最稳定的初始互变异构体（1H-或2H-吡唑）的吡唑环的NH和非质子化氮原子上。通过使用DFT计算进行预测。
京公网安备 11010802027423号