Nitrosation of β′-hydroxylamino-α,β-unsaturated oximes:: synthesis of 1,7-dioxa-2,6-diaza-spiro[4,4]nona-2,8-diene ring system

被引：9

作者：

Amarasekara, AS ^{[1
]}

机构：

[1] Prairie View A&M Univ, Dept Chem, Prairie View, TX 77446 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 15期

关键词：

nitrosation; alpha; beta-unsaturated oximes; pyrazolone; dihydroisoxazole;

D O I：

10.1016/j.tetlet.2005.02.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrosation of bis arylidene acetone oximes with nitrous acid in glacial acetic acid gives 3-vinyl pyrazolone-N,N'-dioxides in 32-37% yield. Similar reactions of 2-arylidenc-6-(hydroxylamino-aryl-methyl)-cyclohexanone oximes give tricyclic compounds with dioxa-2,6-diaza-spiro[4,4]nona-2,8-diene ring systems in 77-84% yield. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2635 / 2638

页数：4

共 14 条

[1] SYNTHESIS AND CYTOTOXIC EVALUATION OF SOME 6-ARYLIDENE-2-(ALPHA-HYDROXYAMINO-ALPHA-ARYLMETHYL)CYCLOHEXANONE OXIMES AND RELATED-COMPOUNDS [J].

DIMMOCK, JR ;

SIDHU, KK ;

QUAIL, JW ;

JIA, Z ;

DUFFY, MJ ;

REID, RS ;

KIRKPATRICK, DL ;

ZHU, L ;

FLETCHER, SM .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1992, 81 (11) :1059-1064

[2] SYNTHESIS AND CYTOTOXIC EVALUATION OF SOME CYCLIC ARYLIDENE KETONES AND RELATED OXIMES, OXIME ESTERS, AND ANALOGS [J].

DIMMOCK, JR ;

SIDHU, KK ;

CHEN, M ;

LI, J ;

QUAIL, JW ;

ALLEN, TM ;

KAO, GY .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1994, 83 (06) :852-858

[3] NITROSATION OF ALPHA,BETA-UNSATURATED OXIMES .5. SYNTHESIS AND CHEMISTRY OF 1-HYDROXYPYRAZOLE 2-OXIDES [J].

FREEMAN, JP ;

GANNON, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (01) :194-&

[4] NITROSATION OF ALPHA,BETA-UNSATURATED OXIMES .4. SYNTHESIS AND STRUCTURE OF 3,4-DIAZACYCLOPENTADIENONE DERIVATIVES [J].

FREEMAN, JP ;

GANNON, JJ ;

SURBEY, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (01) :187-&

[5] CYCLOADDITION REACTIONS OF 3,4-DIAZACYCLOPENTADIENONE OXIDES WITH OLEFINS AND ACETYLENEDICARBOXYLIC ESTER [J].

FREEMAN, JP ;

HOARE, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (01) :19-&

[6]

FREEMAN JR, 1967, TETRAHEDRON LETT, V49, P4917

[7]

HARRIES C, 1921, ANN CHIM, V330, P237

[8] AN ALDOL CONDENSATION EXPERIMENT USING A NUMBER OF ALDEHYDES AND KETONES [J].

HATHAWAY, BA .

JOURNAL OF CHEMICAL EDUCATION, 1987, 64 (04) :367-368

[9]

HENRY P, 1893, BER, V26, P997

[10] RuCl3 catalyses aldol condensations of aldehydes and ketones [J].

Iranpoor, N ;

Kazemi, F .

TETRAHEDRON, 1998, 54 (32) :9475-9480

← 1 2 →