TANDEM AND SELECTIVE CONVERSION OF TETRAHYDROPYRANYL AND SILYL ETHERS TO OXIMES CATALYZED WITH TRICHLOROISOCYANURIC ACID

被引：3

作者：

Aghapour, Ghasem ^{[1
]}

Abbaszadeh, Zeinab ^{[1
]}

机构：

[1] Damghan Univ, Sch Chem, Damghan 36715364, Iran

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2015年 / 190卷 / 09期

关键词：

Tetrahydropyranyl ether; silyl ether; oxime; trichloroisocyanuric acid; tandem synthesis; FACILE CONVERSION; PRIMARY AMIDES; EFFICIENT; ALCOHOLS; ALDEHYDES; ALDOXIMES; NITRILES; MILD; 6-DICYANOBENZOQUINONE; 3-DICHLORO-5;

D O I：

10.1080/10426507.2014.990015

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Direct and oxidative conversion of tetrahydropyranyl and silyl ethers to oximes is described using trichloroisocyanuric acid (TCCA) as a relatively stable and inexpensive oxidant surprisingly in a catalytic amount and hydroxylamine hydrochloride under solvent-free conditions. Oximes can be synthesized from these protected alcohols in the presence of some other functional groups with excellent chemoselectivity using the present tandem catalytic method.

引用

收藏

页码：1464 / 1470

页数：7

相关论文

共 32 条

[1]

Aghapour G, 2007, INDIAN J CHEM B, V46, P649

[2] Selective Tandem Synthesis of Oximes from Benzylic Alcohols Catalyzed with 2, 3-Dichloro-5, 6-dicyanobenzoquinone [J].

Aghapour, Ghasem ;

Mohamadian, Samaneh .

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (04) :1209-1212

[3] CHLORINATION OF OXIMES .1. REACTION AND MECHANISM OF CHLORINATION OF OXIMES IN COMMERCIAL CHLOROFORM AND METHYLENE CHLORIDE [J].

CHIANG, YH .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (15) :2146-&

[4] A simple synthesis of oximes [J].

Damljanovic, I ;

Vukicevic, M ;

Vukicevic, RD .

MONATSHEFTE FUR CHEMIE, 2006, 137 (03) :301-305

[5] Facile preparation of 3,7-diazabicyclo [3.3.0]octane and 3,7,10-triheterocyclic [3.3.3]propellane ring systems from 1,5-diazacyclooctane 3,7-derivatives [J].

Dave, PR ;

Forohar, F ;

Axenrod, T ;

Das, KK ;

Qi, L ;

Watnick, C ;

Yazdekhasti, H .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :8897-8903

[6]

Donaruma L.G., 1960, ORG REACT, V11, P1, DOI DOI 10.1002/0471264180.OR011.01

[7] Regioselective Synthesis of Z-Aldoximes Catalyzed By H3PMo12O40 under Solvent-Free Conditions [J].

Eshghi, Hossein ;

Alizadeh, Mohammad Hasan ;

Davamdar, Ehsan .

JOURNAL OF THE KOREAN CHEMICAL SOCIETY-DAEHAN HWAHAK HOE JEE, 2008, 52 (01) :52-56

[8] TiO2/SO42-:: an efficient and convenient catalyst for preparation of aromatic oximes [J].

Guo, JJ ;

Jin, TS ;

Zhang, SL ;

Li, TS .

GREEN CHEMISTRY, 2001, 3 (04) :193-195

[9] 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate: a mild and efficient oxidant for the cleavage of oxime double bonds under anhydrous conditions [J].

Hajipour, AR ;

Mahboubghah, N .

JOURNAL OF CHEMICAL RESEARCH, 1998, (03) :122-123

[10] A rapid and facile conversion of primary amides and aldoximes to nitriles and ketoximes to amides with triphenylphosphine and N-chlorosuccinimide [J].

Iranpoor, N ;

Firouzabadi, H ;

Aghapour, G .

SYNTHETIC COMMUNICATIONS, 2002, 32 (16) :2535-2541

← 1 2 3 4 →