1,2-vs 1,4-addition of acylbenzotriazoles to α,β-unsaturated aldehydes and ketones.: A novel route to 3-alkyl-4,6-diaryl-3,4-dihydropyran-2-ones

被引：23

作者：

Katritzky, AR ^{[1
]}

Denisko, OV ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 09期

关键词：

D O I：

10.1021/jo011082s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithiation of aliphatic 1-acylbenzotriazoles with subsequent reaction with alpha,beta-unsaturated ketones,13 and aldehydes affords either 3,4,6-trisubstituted 3,4-dihydropyran-2-ones or 1,3-dienes depending on the carbonyl reagent used. Substituent effects on product yield and isomer ratio are discussed.

引用

页码：3104 / 3108

页数：5

共 22 条

[1] Tandem [2+2] cycloaddition-cycloreversion reactions in highly polar media: A convergent one-pot entry to substituted alkenes and dienes [J].

Arrastia, I ;

Cossio, FP .

TETRAHEDRON LETTERS, 1996, 37 (39) :7143-7146

[2]

BAUDIN JB, 1993, B SOC CHIM FR, V130, P856

[3] HALOGENATED KETENES .36. REACTIONS OF CHLOROKETENES WITH KETENE ACETALS [J].

BRADY, WT ;

WATTS, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (20) :4047-4050

[4] ORGANOMETALLICS DERIVED FROM THIOAMIDES .2. REACTION WITH ALPHA-ENONES [J].

GOASDOUE, C ;

GOASDOUE, N ;

GAUDEMAR, M ;

MLADENOVA, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 226 (03) :209-215

[5] REGIOSELECTIVITY OF S-SILYLKETENE S,N ACETALS AND TITANIUM - (ATE) - ENETHIOLATES ADDITION TO UNSATURATED-KETONES [J].

GOASDOUE, C ;

GOASDOUE, N ;

GAUDEMAR, M .

TETRAHEDRON LETTERS, 1984, 25 (05) :537-540

[6]

Hepworth J.D., 1984, COMPREHENSIVE HETERO, V3, P737, DOI DOI 10.1016/B978-008096519-2.00046-1

[7]

Hepworth J. D., 1996, COMPREHENSIVE HETERO, V5, P351, DOI DOI 10.1016/B978-008096518-5.00111-8

[8] INTERMEDIATES FOR THE SYNTHESIS OF OPTICALLY ACTIVE METHYL-SUBSTITUTED LONG-CHAIN ACIDS .3. [J].

HOLLIDAY, IA ;

POLGAR, N .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (JUL) :2934-2936

[9] FLUORIDE ANION INDUCED NOVEL REACTION OF ALPHA-(SULFONIO)KETONE TRIFLATE [J].

ITO, Y ;

NAKAJO, E ;

SHO, K ;

TAMAO, K .

TETRAHEDRON LETTERS, 1987, 28 (20) :2247-2250

[10] Efficient general synthesis of 1-(benzotriazol-1-yl)alkyl esters [J].

Katritzky, AR ;

Pastor, A ;

Voronkov, MV .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (03) :777-781

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