A convenient method for preparation of 2-amino-4,6-diphenylnicotinonitrile using HBF4 as an efficient catalyst via an anomeric based oxidation: A joint experimental and theoretical study

被引：28

作者：

Zolfigol, Mohammad Ali ^{[1
]}

Kiafar, Mahya ^{[1
]}

Yarie, Meysam ^{[1
]}

Taherpour, Avat ^{[2
,3
]}

Fellowes, Thomas ^{[4
]}

Hancok, Amber Nicole ^{[4
,5
]}

Yari, Ako ^{[2
]}

机构：

[1] Bu Ali Sina Univ, Dept Organ Chem, Fac Chem, POB 6517838683, Hamadan, Iran

[2] Razi Univ, Dept Organ Chem, POB 67149-67346, Kermanshah, Iran

[3] Kermanshah Univ Med Sci, Med Biol Res Ctr, Kermanshah, Iran

[4] Univ Melbourne, Sch Chem, Parkville, Vic 3010, Australia

[5] Univ Melbourne, Inst Bio21, Parkville, Vic 3052, Australia

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2017年 / 1137卷

基金：

美国国家科学基金会;

关键词：

HBF4; 2-Amino-4,6-diphenylnicotinonitrile; Anomeric based oxidation; Experimental and theoretical study; Solvent free conditions; ONE-POT SYNTHESIS; DERIVATIVES; IRRADIATION; ORTHOAMIDES; REACTIVITY; INHIBITORS; DISCOVERY; HYDROGEN; SYSTEMS;

D O I：

10.1016/j.molstruc.2017.02.083

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Experimental and computational studies in the synthesis of 2-amino-4,6-diphenylnicotinonitrile using HBF4 as an oxidizing promoter catalyst under mild and solvent free conditions were carried out. The suggested anomeric based oxidation (ABO) mechanism is supported by experimental and theoretical evidence. The theoretical study shows that the intermediate isomers with 5R- and 5S- chiral positions have suitable structures for the aromatization through an anomeric based oxidation in the final step of the mechanistic pathway. (C) 2017 Elsevier B.V. All rights reserved.

引用

页码：674 / 680

页数：7

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