REACTION OF 2-NITRO-2-CYCLOHEXENONE ACETALS AND 3-NITRO-2-CYCLOHEXENONE ACETALS - PREPARATION OF USEFUL INTERMEDIATES

被引：14

作者：

VANKAR, YD

BAWA, A

KUMARAVEL, G

机构：

[1] Department of Chemistry Indian Institute of Technology, Kanpur

来源：

TETRAHEDRON | 1991年 / 47卷 / 10-11期

关键词：

D O I：

10.1016/S0040-4020(01)96113-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Preparation of 2-nitro-2-cyclohexenone acetal 31 starting from 2-nitrocyclohexanone acetal 29 has been reported for the first time. This compound as well as 3-nitro-2-cyclohexenone acetal 1, whose synthesis has been reported by us earlier, react with a variety of nucleophiles to form highly functionalised intermediates. One of them viz. 21 is converted into a bicyclic proportional-methylene-gamma-lactone 24 using radical chemistry.

引用

收藏

页码：2027 / 2040

页数：14

相关论文

共 20 条

[1] PREPARATION AND SYNTHETIC UTILITY OF 1-PHENYLTHIO-1-NITRO EPOXIDES - FACILE PREPARATION OF ALPHA-SUBSTITUTED S-PHENYL THIO ESTERS [J].

ASHWELL, M ;

JACKSON, RFW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) :282-283

[2] STEREOSPECIFIC SYNTHESIS OF THE LYTHGOE RING A ALDEHYDE FOR THE PREPARATION OF 1-ALPHA-HYDROXYLATED TACHYSTEROLS AND CALCIFEROLS [J].

BAGGIOLINI, EG ;

HENNESSY, BM ;

IACOBELLI, JA ;

USKOKOVIC, MR .

TETRAHEDRON LETTERS, 1987, 28 (19) :2095-2098

[3] STEROIDS .120. SYNTHESIS OF HALOGENATED STEROID HORMONES - NEW ROUTES TO 6-ALPHA-FLUOROTESTOSTERONE AND THE 6-ALPHA-FLUORO AND 6-BETA-FLUORO ANALOGS OF PROGESTERONE - THE SYNTHESIS OF 6-ALPHA-FLUORO AND 6-BETA-FLUORO REICHSTEINS COMPOUND-S AND 6-ALPHA-FLUORODESOXYCORTICOSTERONE AND 6-BETA-FLUORODESOXYCORTICOSTERONE ACETATE [J].

BOWERS, A ;

IBANEZ, LC ;

RINGOLD, HJ .

TETRAHEDRON, 1959, 7 (1-2) :138-152

[4] 3-NITROCYCLOALKENONES, SYNTHESIS AND USE AS REVERSE AFFINITY CYCLOALKYNONE EQUIVALENTS [J].

COREY, EJ ;

ESTREICHER, H .

TETRAHEDRON LETTERS, 1981, 22 (07) :603-606

[5] NEW SYNTHESIS OF CONJUGATED NITRO CYCLO OLEFINS, UNUSUALLY VERSATILE SYNTHETIC INTERMEDIATES [J].

COREY, EJ ;

ESTREICHER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (19) :6294-6295

[6] USE OF BETA-PHENYLSULFINYL-ALPHA,BETA-UNSATURATED CARBONYL DIENOPHILES IN DIELS-ALDER REACTIONS [J].

DANISHEFSKY, S ;

HARAYAMA, T ;

SINGH, RK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) :7008-7012

[7] DIELS-ALDER REACTIONS OF TRANS-1-METHOXY-3-TRIMETHYLSILYLOXY-1,3-BUTADIENE [J].

DANISHEFSKY, S ;

KITAHARA, T ;

YAN, CF ;

MORRIS, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) :6996-7000

[8] CYCLOALK-2-ENONES AND ALPHA,BETA,ALPHA',BETA'-CYCLOALKADIENONES .A. SYNTHESIS .B. ON DIRECTION OF BROMINATION OF 2-SUBSTITUTED CYCLOALKANONES AND THEIR KETALS [J].

GARBISCH, EW .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (07) :2109-&

[9]

HUET F, 1978, SYNTHESIS-STUTTGART, P63

[10]

Jones H, 1980, Fortschr Chem Org Naturst, V39, P63