Oxidation of hydrazones by hypervalent organoiodine reagents: Regeneration of the carbonyl group and facile syntheses of alpha-acetoxy and alpha-alkoxy azo compounds

被引：45

作者：

Barton, DHR ^{[1
]}

Jaszberenyi, JC ^{[1
]}

Liu, WS ^{[1
]}

Shinada, T ^{[1
]}

机构：

[1] TECH UNIV BUDAPEST,RES GRP,HUNGARIAN ACAD SCI,DEPT ORGAN CHEM TECHNOL,H-1111 BUDAPEST,HUNGARY

来源：

TETRAHEDRON | 1996年 / 52卷 / 47期

关键词：

D O I：

10.1016/0040-4020(96)00940-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various hydrazone derivatives of alpha-keto esters were prepared. The carbonyl group was readily regenerated in high yield from phenylhydrazones through oxidative hydrolysis using hypervalent organoiodine(III) reagents-either bis(trifluoroacetoxy)-iodobenzene (BTIB) in aqueous acetonitrile or hydroxy (tosyloxy)iodobenzene (HTIB) in chloroform, alpha-Acetoxy phenyl- or methylazo compounds were readily synthesized by oxidation of the corresponding hydrazones with iodobenzene diacetate (IBDA) in dichloromethane or acetic acid. alpha-Methoxy phenyl- or methylazo compounds were also prepared by oxidation of the hydrazones in methanol. The mechanisms of the oxidation reactions are discussed. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：14673 / 14688

页数：16

共 58 条

[31] REACTIONS OF LEAD TETRA-ACETATE .5. SYNTHESIS OF 1-PHENYLINDAZOLE AND SOME DERIVATIVES PYRIDYLINDAZOLES AND THIENOPYRAZOLES [J].

GLADSTONE, WA ;

NORMAN, ROC .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (17) :1527-+

[32]

Greenne T.W., 1991, PROTECTIVE GROUPS OR, P212

[33] OXIDATION BY SINGLET OXYGEN OF ARYLAZONAPHTHOLS EXHIBITING AZO-HYDRAZONE TAUTOMERISM [J].

GRIFFITHS, J ;

HAWKINS, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1977, (06) :747-752

[34] REACTIONS OF LEAD TETRA-ACETATE .9. MECHANISM OF REACTION WITH KETONE ARYLHYDRAZONES [J].

HARRISON, MJ ;

NORMAN, ROC ;

GLADSTON.WA .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (08) :735-&

[35] PREPARATION AND STRUCTURE OF AZOACETATES, A NEW CLASS OF COMPOUNDS [J].

IFFLAND, DC ;

SALISBURY, L ;

SCHAFER, WR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (03) :747-&

[36] GEOMETRICAL ISOMERISM OF PHENYLHYDRAZONES OF ALPHA-KETO ESTERS .2. PARA-SUBSTITUTED PHENYLHYDRAZONES OF ETHYL PYRUVATE AND 2,4-DINITROPHENYLHYDRAZONES OF SOME ALPHA-KETO ESTERS [J].

ISHIBASHI, F ;

NASHIMA, T ;

NISHINO, J ;

KOBAYASHI, I ;

ICHIHARA, Y ;

KITAGAWA, Y ;

SASAKI, S ;

YOSHIKAWA, M ;

MATSUOKA, A ;

YAMAMOTO, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (01) :73-76

[37] MONOSUBSTITUTED DIAZENES (DIIMIDES) - SURPRISING INTERMEDIATES [J].

KOSOWER, EM .

ACCOUNTS OF CHEMICAL RESEARCH, 1971, 4 (06) :193-&

[38] REGENERATION OF KETONES FROM TOSYLHYDRAZONES, ARYLHYDRAZONES, AND OXIMES BY EXCHANGE WITH ACETONE [J].

MAYNEZ, SR ;

PELAVIN, L ;

ERKER, G .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (22) :3302-3303

[39]

MESTER L, 1963, METHODS CARBOHYDRATE, V2, P117

[40]

MORIARTY RM, 1993, SYNTHESIS-STUTTGART, P318

← 1 2 3 4 5 6 →