A computational study on the [3+2] cycloaddition of para-quinone methides with nitrile imines: a two-stage one-step mechanism

被引：9

作者：

Soleymani, Mousa ^{[1
]}

Jahanparvar, Sahar ^{[1
]}

机构：

[1] Ayatollah Boroujerdi Univ, Fac Sci, Chem Dept, Boroujerd, Iran

来源：

MONATSHEFTE FUR CHEMIE | 2020年 / 151卷 / 01期

关键词：

Pyrazoline; Spiro compounds; Reaction mechanisms; Fukui functions; Electron transfer; DFT; DOUBLE 1,3-DIPOLAR CYCLOADDITION; QUANTITATIVE CHARACTERIZATION; ANTIMICROBIAL EVALUATION; MOLECULAR-MECHANISM; DFT; ELECTROPHILICITY; PYRAZOLINES; REGIOSELECTIVITY; THIOPYRIMIDINE; NITRILIMINES;

D O I：

10.1007/s00706-019-02531-2

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the present work, the [3+2] cycloaddition reaction of para-quinone methides and nitrile imines, experimentally researched by Su and coworkers, is studied using density functional theory. A good agreement is observed between the experimental finding and the results obtained from the Fukui functions and potential energy surface analyses. Also, we found that the reaction is relatively polar in character and takes place via a two-stage one-step mechanism. Graphic abstract

引用

页码：51 / 61

页数：11

共 43 条

[1] A computational study on the [3+2] cycloaddition of para-quinone methides with nitrile imines: a two-stage one-step mechanism
Mousa Soleymani
Sahar Jahanparvar
Monatshefte für Chemie - Chemical Monthly, 2020, 151 : 51 - 61
[2] [3+2] Cycloaddition of para-Quinone Methides with Nitrile Imines: Approach to Spiro-pyrazoline-cyclohexadienones
Su, Yingpeng
Zhao, Yanan
Chang, Bingbing
Zhao, Xiaolong
Zhang, Rong
Liu, Xuan
Huang, Danfeng
Wang, Ke-Hu
Huo, Congde
Hu, Yulai
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11): : 6719 - 6728
[3] Synthesis of Pyrrolo[1,2-α]indoles via (3+2)-Annulations of (Aza)-para-Quinone Methides with Indoles
Zhang, Xiang-Zhi
Qiu, Zong-Wang
Wen, Gui-Hua
Ma, Ai-Jun
Bao, Peng-Jin
Du, Ji-Yuan
Xu, Xue-Tao
Feng, Na
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SYNTHESIS-STUTTGART, 2020, 52 (23): : 3640 - 3649
[4] SYNTHESIS OF DIHYDRO-1H-INDENES VIA A FORMAL 3+2-CYCLOADDITION OF PARA-QUINONE METHIDES AND STYRENES
ANGLE, SR
ARNAIZ, DO
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12): : 3708 - 3710
[5] [4+2]-Cycloaddition of para-Quinone Methides with Hexahydro-1,3,5-Triazines: Access to 1,3-Benzoxazine Derivatives
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Zhou, Shuang-Jing
Xu, Guo-Yong
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ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (03) : 523 - 527
[6] Quadruple Functionalized Pyrazole Pharmacophores by One-pot Regioselective [3+2] Cycloaddition of Fluorinated Nitrile Imines and Dicyanoalkenes
Zhou, Yin
Gao, Cheng-Feng
Ma, Hai
Nie, Jing
Ma, Jun-An
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CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (15)
[7] Metal-Free Approach for Oxa-spirocyclohexadienones through [3+2]/[4+2] ipso-Cyclization of para-Quinone Methides with Halo Alcohols
Gaikwad, Ramesh A.
Savekar, Amol T.
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JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (14): : 9987 - 10001
[8] A DFT study of the mechanism and the regioselectivity of [3+2] cycloaddition reactions of nitrile oxides with α,β-acetylenic aldehyde
Sobhi, Chafia
Nacereddine, Abdelmalek Khorief
Nasri, Lilia
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MOLECULAR PHYSICS, 2016, 114 (21) : 3193 - 3200
[9] [3+2] Cycloaddition reaction of disubstituted-3-benzylidene succinimide with C, N-disubstituted nitrile imines for synthesizing spiro-heterocycles: A computational study
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Kwawu, Caroline R.
Menkah, Elliot S.
Adei, Evans
COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2023, 1225
[10] (3+2)-Cycloadditions of Levoglucosenone (LGO) with Fluorinated Nitrile Imines Derived from Trifluoroacetonitrile: An Experimental and Computational Study
Mloston, Grzegorz
Urbaniak, Katarzyna
Palusiak, Marcin
Witczak, Zbigniew J.
Wuerthwein, Ernst-Ulrich
MOLECULES, 2023, 28 (21):

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