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在亲核芳基取代反应中,通过亲核和亲电溶剂化作用激活亲电试剂/亲核试剂对。

Activation of Electrophile/Nucleophile Pair by a Nucleophilic and Electrophilic Solvation in a SAr Reaction.

作者信息

Sánchez Bruno, Calderón Cristian, Tapia Ricardo A, Contreras Renato, Campodónico Paola R

机构信息

Departamento de Química, Facultad de Ciencias, Universidad de Chile, Santiago, Chile.

Centro de Química Médica, Facultad de Medicina, Clínica Alemana Universidad del Desarrollo, Santiago, Chile.

出版信息

Front Chem. 2018 Oct 23;6:509. doi: 10.3389/fchem.2018.00509. eCollection 2018.

DOI:10.3389/fchem.2018.00509
PMID:30406087
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6206274/
Abstract

Nucleophilic aromatic substitution reactions of 4-chloroquinazoline toward aniline and hydrazine were used as a model system to experimentally show that a substrate bearing heteroatoms on the aromatic ring as substituent is able to establish intramolecular hydrogen bond which may be activated by the reaction media and/or the nature of the nucleophile.

摘要

以4-氯喹唑啉与苯胺和肼的亲核芳香取代反应作为模型体系,通过实验表明,在芳香环上带有杂原子作为取代基的底物能够形成分子内氢键,该氢键可能会被反应介质和/或亲核试剂的性质所激活。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03bf/6206274/a58a4010a531/fchem-06-00509-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03bf/6206274/a2d80eb8f49c/fchem-06-00509-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03bf/6206274/779cd2838a74/fchem-06-00509-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03bf/6206274/90ed0f6e6936/fchem-06-00509-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03bf/6206274/6646c226d8d7/fchem-06-00509-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03bf/6206274/08ecad652e60/fchem-06-00509-g0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03bf/6206274/a58a4010a531/fchem-06-00509-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03bf/6206274/a2d80eb8f49c/fchem-06-00509-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03bf/6206274/779cd2838a74/fchem-06-00509-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03bf/6206274/90ed0f6e6936/fchem-06-00509-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03bf/6206274/6646c226d8d7/fchem-06-00509-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03bf/6206274/08ecad652e60/fchem-06-00509-g0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/03bf/6206274/a58a4010a531/fchem-06-00509-g0002.jpg

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2
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J Phys Chem B. 2015 Oct 15;119(41):13160-6. doi: 10.1021/acs.jpcb.5b05305. Epub 2015 Oct 1.
3
Chemical characteristics, synthetic methods, and biological potential of quinazoline and quinazolinone derivatives.
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