Studies of Stereochemistry of 3-(Arylhydrazono)Furan-2(3De)-Ones, Synthesis of 4-(Arylhydrazono)Pyridazin-3(1De)-Ones

被引：13

作者：

Maiorova, Oksana A. ^{[1
]}

Babkina, Natalya V. ^{[1
]}

Egorova, Alevtina Yu. ^{[1
]}

机构：

[1] NG Chernyshevsky Saratov State Univ, Saratov 410012, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2015年 / 51卷 / 06期

基金：

俄罗斯科学基金会; 俄罗斯基础研究基金会;

关键词：

4-(arylhydrazono)-4,5-dihydropyridazin-3(2H)-one; 3-(arylhydrazono) furan-2(3H)-one; azo-hydrazone tautomerism; Z/E-isomers; NMR spectroscopy; SELECTIVITY;

D O I：

10.1007/s10593-015-1730-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The structural characteristics of 5-aryl-3-(arylhydrazono)furan-2(3De)-ones accessed via azocoupling of furan-2(3De)-ones with aryldiazonium salts were established by NMR spectroscopy (including two-dimensional NMR experiments H-1-C-13 HMQC, H-1-N-15 HMQC, H-1-C-13 HMBC, NOE) and X-ray structural analysis techniques. The reaction of synthesized compounds with hydrazine leading to the formation of six-membered heterocycles, hydrazono-substituted 4,5-dihydropyridazin-3(2De)-ones, was studied.

引用

页码：514 / 517

页数：4

共 15 条

[1] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].

ALLEN, FH ;

KENNARD, O ;

WATSON, DG ;

BRAMMER, L ;

ORPEN, AG ;

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19

[2] Reactions of 5-mercaptoazoles and pyridine-2-thiones with acetylenic esters. Selectivity of the formation of novel fused thiazin-4-ones and thiazolidin-4-ones [J].

Bakulev, VA ;

Berseneva, VS ;

Belskaia, NP ;

Morzherin, YY ;

Zaitsev, A ;

Dehaen, W ;

Luyten, I ;

Toppet, S .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (01) :134-139

[3] Synthesis and properties of hydrazones bearing amide, thioamide and amidine functions [J].

Belskaya, Nataliya P. ;

Dehaen, Wim ;

Bakulev, Vasiliy A. .

ARKIVOC, 2010, :275-332

[4] Chemistry of carbofunctionally substituted hydrazones [J].

Elassar, Abdel-Zaher A. ;

Dib, Hicham H. ;

Al-Awadi, Nouria A. ;

Elnagdi, Mohammad H. .

ARKIVOC, 2007, :272-315

[5] REACTIONS WITH ARYLHYDRAZONES OF ALPHA-CYANOKETONES - STRUCTURE OF "2-ARYLHYDRAZONO-3-KETIMINO-NITRILES [J].

ELNAGDI, MH ;

SALLAM, MMM ;

FAHMY, HM ;

IBRAHIM, SAM ;

ELIAS, MAM .

HELVETICA CHIMICA ACTA, 1976, 59 (02) :551-557

[6] PYRIMIDINE-DERIVATIVES AND RELATED COMPOUNDS II - SYNTHESIS OF SOME DERIVATIVES OF PYRIMIDO[1,2-2',3']PYRAZOLO-[1,5-A]PYRIMIDINES, A NEW RING-SYSTEM [J].

ELNAGDI, MH ;

SALLAM, MMM ;

ILIAS, MAM .

HELVETICA CHIMICA ACTA, 1975, 58 (07) :1944-1949

[7] Azo coupling of 5-substituted furan-2(3H)-ones and 1H-pyrrol-2(3H)-ones with arene(hetarene)diazonium salts [J].

Gavkus, D. N. ;

Maiorova, O. A. ;

Borisov, M. Yu ;

Egorova, A. Yu .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (09) :1229-1232

[8] The synthesis, antimicrobial activity and absorption characteristics of some novel heterocyclic disazo dyes [J].

Karci, Fikret ;

Sener, Nesrin ;

Yamac, Mustafa ;

Sener, Izzet ;

Demircali, Aykut .

DYES AND PIGMENTS, 2009, 80 (01) :47-52

[9] STRUCTURE OF DIAZONIUM COUPLING PRODUCTS OF GAMM-PHENYL-DELTABETA,GAMMA-BUTENOLIDE [J].

KHATTAB, SA ;

SHAWALI, SA ;

FARAG, AM .

JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1977, 22 (01) :104-110

[10] 4-arylazo-3,5-diamino-1H-pyrazole CDK inhibitors:: SAR study, crystal structure in complex with CDK2, selectivity, and cellular effects [J].

Krystof, Vladimir ;

Cankar, Petr ;

Frysova, Iveta ;

Slouka, Jan ;

Kontopidis, George ;

Dzubak, Petr ;

Hajduch, Marian ;

Srovnal, Josef ;

de Azevedo, Walter F., Jr. ;

Orsag, Martin ;

Paprskarova, Martina ;

Rolcik, Jakub ;

Latr, Ales ;

Fischer, Peter M. ;

Strnad, Miroslav .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (22) :6500-6509

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