Features of the reactions of β-aryl(heteryl)-α-nitroacrylates with N,N-, N,O-, and N,S-binucleophiles

被引：2

作者：

Baichurina, L. V. ^{[1
]}

Baichurin, R. I. ^{[1
]}

Filippenko, M. V. ^{[1
]}

Aboskalova, N. I. ^{[1
]}

Berestovitskaya, V. M. ^{[1
]}

机构：

[1] Herzen State Pedag Univ Russia, St Petersburg 191186, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2012年 / 82卷 / 08期

关键词：

2-ARYLBENZOTHIAZOLES; CONDENSATION; IRRADIATION; DERIVATIVES; ALDEHYDES; ACID;

D O I：

10.1134/S1070363212080117

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reactions of beta-aryl(heteryl)-alpha-nitroacrylates with N,N-, N,O-, and N,S-binucleophiles proceed regiospecifically through the initial formation of the Ad(N) products, among which only the product from o-aminothiophenol was isolated. The conditions of converting the S-adducts into 2-aryl(heteryl)benzothiazole were found. The N-adducts formed in the reaction with hydrazine, o-phenylenediamine, and o-aminophenol undergo immediately the spontaneous transformation into the linear (azine, azomethine) or heterocyclic (benzimidazole) structures.

引用

页码：1400 / 1408

页数：9

共 30 条

[1] β-Acetyl-β-Nitrostyrenes: Structure and Use for Synthesis of Heteryl-containing Structures [J].

Aboskalova, N. I. ;

Smirnova, N. N. ;

Kataeva, O. N. ;

Baichurin, R. I. ;

Fel'gendler, A. V. ;

Berkova, G. A. ;

Berestovitskaya, V. M. .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (09) :1711-1718

[2]

Aboskalova N.I., 2002, CHEM HETEROCYCLIC CH, V10, P1291

[3]

Aboskalova N.I., 1978, 31 GERTS CHT MET SIN, P86

[4] Copper(I)-promoted palladium-catalyzed cross-coupling of unsaturated tri-n-butylstannane with heteroaromatic thioether [J].

Alphonse, FA ;

Suzenet, F ;

Keromnes, A ;

Lebret, B ;

Guillaumet, G .

ORGANIC LETTERS, 2003, 5 (06) :803-805

[5] Acetic acid-promoted condensation of o-phenylenediamine with aldehydes into 2-aryl-1-(arylmethyl)-1H-benzimidazoles under microwave irradiation [J].

Azarifar, Davood ;

Pirhayati, Mojgan ;

Maleki, Behrooz ;

Sanginabadi, Mehrangiz ;

Yami, Razieh Nejat .

JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2010, 75 (09) :1181-1189

[6] Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles [J].

Bahrami, Kiumars ;

Khodaei, Mohammad M. ;

Nejati, Akbar .

GREEN CHEMISTRY, 2010, 12 (07) :1237-1241

[7] One-Pot Synthesis of 2-Aryl-4-methyl-3-nitro-2,3-dihydro-1,5-benzothiazepines [J].

Baichurin, R. I. ;

Aboskalova, N. I. ;

Berestovitskaya, V. M. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (10) :1590-1591

[8] Synthesis of pyrrole- and indole-containing nitropropanoates on the basis of β-heteryl-α-nitroacrylates [J].

Baichurina, L. V. ;

Baichurin, R. I. ;

Aboskalova, N. I. ;

Berestovitskaya, V. M. .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2010, 80 (10) :2022-2026

[9] Geminal Acylnitrostyrenes in the Reaction with ortho-Aminothiophenol [J].

Berestovitskaya, V. M. ;

Baichurin, R. I. ;

Aboskalova, N. I. ;

Lysenko, K. A. ;

Anan'ev, I. V. .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2011, 81 (06) :1163-1170

[10] PHOTOCHEMISTRY OF UNSATURATED NITROGEN-CONTAINING COMPOUNDS .3. MECHANISM OF CIS- AND TRANS-STILBENE FORMATION FROM IRRADIATION OF BENZALAZINE [J].

BINKLEY, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (04) :931-&

← 1 2 3 →