INTRAMOLECULAR OXIDATIVE CYCLIZATION OF 1-(4-HYDROXYARYL)-2-KETOXIMES 4-HOARCH2C(=NOH)R WITH PHENYLIODINE(III) BIS(TRIFLUOROACETATE)

被引：55

作者：

KACAN, M ^{[1
]}

KOYUNCU, D ^{[1
]}

MCKILLOP, A ^{[1
]}

机构：

[1] UNIV E ANGLIA,SCH CHEM SCI,NORWICH NR4 7TJ,NORFOLK,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 15期

关键词：

D O I：

10.1039/p19930001771

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 1-(4-hydroxyaryl)-2-ketoximes, 4-HOArCH2C(=NOH)R, with phenyliodine(III) bis(trifluoroacetate) in acetonitrile at 0-degrees-C results in smooth intramolecular oxidative cyclisation and formation of 1-oxa-2-azaspiro[4.5]deca-2,6,9-trien-8-ones in good to excellent yield. Attempted application of the procedure to 1-(2-hydroxyphenyl)propan-2-one oxime resulted in formation of the [4 + 2] dimer of the initially formed spiroisoxazoline.

引用

页码：1771 / 1776

页数：6

共 26 条

[1] NEUE VERBINDUNGEN MIT DEM GRUNDSKELETT SYNTHETISCHER OESTROGENE, 6.MITT. - SYNTHESE DES 3,4-BIS-(P-HYDROXYPHENYL)-HEXANDIONS-(2,5) UND VERWANDTER VERBINDUNGEN
BRETSCHNEIDER, H
LUTZ, R
[J]. MONATSHEFTE FUR CHEMIE UND VERWANDTE TEILE ANDERER WISSENSCHAFTEN, 1964, 95 (06): : 1702 - +
[2] THE BROMO-COMPOUNDS OF THE TRUE SPONGE VERONGIA-AEROPHOBA
CIMINO, G
DEROSA, S
DESTEFANO, S
SELF, R
SODANO, G
[J]. TETRAHEDRON LETTERS, 1983, 24 (29) : 3029 - 3032
[3] INTRAMOLECULAR CYCLIZATION OF PHENOLIC OXIMES .1. CYCLIZATIONS WITH MANGANESE(III) TRIS(ACETYLACETONATE)
FORRESTER, AR
THOMSON, RH
WOO, SO
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (22): : 2340 - 2348
[4] FORRESTER AR, 1987, J CHEM SOC P1, P2348
[5] REACTION OF 2,6-DISUBSTITUTED PHENOLS WITH VINYLLEAD TRIACETATES AND ALK-1-YNYLLEAD TRIACETATES - SYNTHESIS OF 6-VINYL-CYCLOHEXA-2,4-DIENONES AND 6-ALKYNYL-CYCLOHEXA-2,4-DIENONES AND CRYSTAL-STRUCTURE OF 1,3,5,7-TETRAMETHYL-3,5-BIS(PHENYLETHYNYL)-1,3,4,4A,5,8A-HEXAHYDRO-1,4-ETHENONAPHTHALENE-2,6-DIONE
HAMBLEY, TW
HOLMES, RJ
PARKINSON, CJ
PINHEY, JT
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (15): : 1917 - 1922
[6] SYN-ANTI ISOMERISM OF PARA-CHLOROBENZALDOXIME WITH BORON FLUORIDE
HAUSER, CR
HOFFENBERG, DS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1955, 20 (11) : 1491 - 1495
[7] Heinzelman R., 1963, ORG SYNTH, V4, P573
[8] TOTAL SYNTHESIS OF DISCORHABDIN-C - A GENERAL AZA SPIRO DIENONE FORMATION FROM O-SILYLATED PHENOL DERIVATIVES USING A HYPERVALENT IODINE REAGENT
KITA, Y
TOHMA, H
INAGAKI, M
HATANAKA, K
YAKURA, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) : 2175 - 2180
[9] HYPERVALENT IODINE OXIDATION OF N-ACYLTYRAMINES - SYNTHESIS OF QUINOL ETHERS, SPIROHEXADIENONES, AND HEXAHYDROINDOL-6-ONES
KITA, Y
TOHMA, H
KIKUCHI, K
INAGAKI, M
YAKURA, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) : 435 - 438
[10] LESPAGNOL A, 1947, B SOC CHIM FR, P480

← 1 2 3 →