Facile aromatisation of Hantzsch 1,4-dihydropyridines by autoxidation in the presence of p-toluenesulfonic acid in acetic acid

被引：3

作者：

Zhang, Ding ^{[1
]}

Sha, Min ^{[2
]}

机构：

[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Jiangsu, Peoples R China

[2] Nanjing Univ Finance & Econ, Sch Management Sci & Engn, Nanjing 210046, Jiangsu, Peoples R China

来源：

JOURNAL OF CHEMICAL RESEARCH | 2018年 / 03期

基金：

中国国家自然科学基金;

关键词：

autoxidation; dehydrogenation; free radicals; heterocycles; catalysis; OXIDATIVE AROMATIZATION; 1,3,5-TRISUBSTITUTED PYRAZOLINES; MOLECULAR-OXYGEN; EFFICIENT; CATALYST; CARBON; MODEL;

D O I：

10.3184/174751918X15208600846791

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple protocol to achieve the aromatisation of Hantzsch dihydropyridines in high yield was established using p-toluenesulfonic acid in acetic acid and yields of 90% were obtained at room temperature. With regards to the Hantzsch 1,4-dihydropyridines derived from alkyl aldehydes bearing one or more a-hydrogens, dealkylation products were obtained through a proposed autoxidation mechanism.

引用

页码：141 / 144

页数：4

共 25 条

[11] Catalytic aromatization of Hantzsch 1,4-dihydropyridines by ferric perchlorate in acetic acid [J].

Heravi, MM ;

Behbahani, FK ;

Oskooie, HA ;

Shoar, RH .

TETRAHEDRON LETTERS, 2005, 46 (16) :2775-2777

[12] A Novel, Facile, Simple and Convenient Oxidative Aromatization of Hantzsch 1,4-Dihydropyridines to Pyridines Using Polymeric Iodosobenzene with KBr [J].

Kumar, Parvin .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (06) :1429-1433

[13]

Love B., 1965, JORG CHEM, V30, P1914

[14] Catalytic oxidation of Hantzsch 1,4-dihydropyridines by RuCl3 under oxygen atmosphere [J].

Mashraqui, SH ;

Karnik, MA .

TETRAHEDRON LETTERS, 1998, 39 (27) :4895-4898

[15] Auto-oxidation [J].

Milas, NA .

CHEMICAL REVIEWS, 1932, 10 (02) :295-364

[16] KEILINS RESPIRATORY-CHAIN CONCEPT AND ITS CHEMIOSMOTIC CONSEQUENCES [J].

MITCHELL, P .

SCIENCE, 1979, 206 (4423) :1148-1159

[17] Oxidative aromatization of 9,10-dihydroanthracenes using molecular oxygen promoted by activated carbon [J].

Nakamichi, N ;

Kawabata, H ;

Hayashi, M .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (21) :8272-8273

[18] Oxidative aromatization of 1,3,5-trisubstituted pyrazolines and hantzsch 1,4-dihydropyridines by Pd/C in acetic acid [J].

Nakamichi, N ;

Kawashita, Y ;

Hayashi, M .

ORGANIC LETTERS, 2002, 4 (22) :3955-3957

[19] Glucose-lowering in a db/db mouse model by dihydropyridine diacid glycogen phosphorylase inhibitors [J].

Ogawa, AK ;

Willoughby, CA ;

Bergeron, R ;

Ellsworth, KP ;

Geissler, WM ;

Myers, RW ;

Yao, J ;

Harris, G ;

Chapman, KT .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (20) :3405-3408

[20] The complex synergy of water in metal/bromide autoxidations. Part II. Effect of water and catalyst on the aerobic oxidation of benzaldehydes and the effect of water on the elementary catalytic pathways [J].

Partenheimer, W .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (04) :580-590

← 1 2 3 →