Understanding the high reactivity of triazolinediones in Diels-Alder reactions. A DFT study

被引：7

作者：

Fernandez-Herrera, Maria A. ^{[1
]}

Zavala-Oseguera, Claudia ^{[2
]}

Luis Cabellos, Jose ^{[2
]}

Sandoval-Ramirez, Jesus ^{[1
]}

Domingo, Luis R. ^{[3
]}

Merino, Gabriel ^{[2
]}

机构：

[1] Benemerita Univ Autonoma Puebla, Fac Ciencias Quim, Puebla 72570, Pue, Mexico

[2] Ctr Invest & Estudios Avanzados, Dept Fis Aplicada, Unidad Merida, Merida 97310, Yuc, Mexico

[3] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain

来源：

JOURNAL OF MOLECULAR MODELING | 2014年 / 20卷 / 04期

关键词：

DFT study; Polar Diels-Alder reaction; Steroidal diene; TADs; STEPWISE MECHANISMS; OXIDATION; 4-PHENYL-1,2,4-TRIAZOLINE-3,5-DIONE; EFFICIENT;

D O I：

10.1007/s00894-014-2207-7

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The participation of 4-substituted-1,2,4-triazoline-3,5-diones (TADs) in Diels-Alder reactions toward a series of dienes is studied at the M05-2X/6-31+G(d,p) level. These reactions show very low activation energies and complete endo selectivity, in agreement with the experimental data. For a dienic steroid model, the reaction presents an a-facial selectivity. Analysis of reactivity indices explains the superelectrophilic character of TADs, and low activation energy. The substituent and solvent effects are also evaluated.

引用

页数：7

共 50 条

[1] Understanding the high reactivity of triazolinediones in Diels-Alder reactions. A DFT study
María A. Fernández-Herrera
Claudia Zavala-Oseguera
José Luis Cabellos
Jesús Sandoval-Ramírez
Luis R. Domingo
Gabriel Merino
Journal of Molecular Modeling, 2014, 20
[2] Understanding the participation of 3-nitropyridine in polar Diels-Alder reactions. A DFT study
Ormachea, Carla M.
Mancini, Pedro M. E.
Kneeteman, Maria N.
Domingo, Luis R.
COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2015, 1072 : 37 - 42
[3] The origin of the high reactivity of triazolinediones (TADs) in Diels-Alder reactions from a theoretical perspective
Rojas-Valencia, Natalia
Nunez-Zarur, Francisco
TETRAHEDRON, 2020, 76 (38)
[4] SUBSTITUENT AND SOLVENT EFFECTS ON DIELS-ALDER REACTIONS OF TRIAZOLINEDIONES
BURRAGE, ME
COOKSON, RC
GUPTE, SS
STEVENS, DR
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (12): : 1325 - 1334
[5] The mechanism of ionic Diels-Alder reactions. A DFT study of the oxa-Povarov reaction
Domingo, Luis R.
Aurell, Maria J.
Perez, Patricia
RSC ADVANCES, 2014, 4 (32) : 16567 - 16577
[6] Rationalizing the Substituent Effects in Diels-Alder Reactions of Triazolinediones with Anthracene
Hernandez-Mancera, Jennifer P.
Rojas-Valencia, Natalia
Nunez-Zarur, Francisco
JOURNAL OF PHYSICAL CHEMISTRY A, 2022, 126 (38): : 6657 - 6667
[7] Understanding the reactivity and selectivity of Diels-Alder reactions involving furans
Alves, Tiago Vinicius
Fernandez, Israel
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (38) : 7767 - 7775
[8] STRUCTURE AND REACTIVITY IN DIELS-ALDER REACTIONS
INUKAI, T
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1971, 29 (04) : 353 - +
[9] Diastereoselective Diels-Alder reactions. The role of the catalyst
Huang, YF
Sonnet, PE
Carroll, PJ
Dalton, DR
TETRAHEDRON LETTERS, 2000, 41 (15) : 2519 - 2522
[10] Theoretical study on the mechanochemical reactivity in Diels-Alder reactions
Sakai, Wakana
Gonnet, Lori
Haruta, Naoki
Sato, Tohru
Baron, Michel
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2024, 26 (02) : 873 - 878

← 1 2 3 4 5 →