THE SYNTHESIS AND CHEMISTRY OF FUNCTIONALIZED FUROCHROMONES .4. ADDITION OF NITRONATE ANIONS TO 3-BROMOCHROMONE AND 6-BROMOFUROCHROMONE - AN EXPEDIENT ROUTE TO FURO(3',2'-6,7)-BENZOPYRANO(2,3-D)-ISOXAZOLONES AND CHROMONO(2,3-D)ISOXAZOLONES

被引：7

作者：

GAMMILL, RB

NASH, SA

BELL, LT

WATT, W

机构：

[1] The Upjohn Laboratories The Upjohn Company, Kalamazoo

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 08期

关键词：

D O I：

10.1016/S0040-4039(00)91842-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of nitronate anions to 3-bromochromone 1 and 6-bromofurochoromone 2 results in the efficient generation of 3-hydroxy-2-(1-(hydroxyimino)alkyl,aryl or carboalkoxy) substituted chromones and the corresponding 6,7-disubstituted furochromones. These compounds are efficiently converted to furo(3',2':6,7)benzopyrano(2,3-d)isoxazoles and chromono(2,3-d)isoxazoles, respectively, with N,N-dimethylformamide dimethylacetal (DMF-DMA).

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页码：993 / 996

页数：4

相关论文

共 18 条

[1]

Baer H.H., 1970, CHEM NITRO NITROSO 2, P75

[2] STUDIES ON METHYLATED 1,2,3-TRIAZOLES .3. [J].

BEGTRUP, M ;

PEDERSEN, C .

ACTA CHEMICA SCANDINAVICA, 1967, 21 (03) :633-&

[3] AZOLIUM ANIONS AND THEIR REACTION WITH ELECTROPHILIC REAGENTS [J].

BEGTRUP, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (09) :334-335

[4] STUDIES ON 4-PYRONES .39. 2-AMINO-3-HYDROXY-CHROMONE [J].

EIDEN, F ;

DOLCHER, D .

ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESSELSCHAFT, 1972, 305 (09) :698-&

[5]

ERASHKO VI, 1966, RUSS CHEM REV, V39, P419

[6] KHELLIN ANALOGS .1. GENERAL TOPOLOGICAL REQUIREMENTS FOR LIPID-ALTERING ACTIVITY IN FUROCHROMONES [J].

GAMMILL, RB ;

DAY, CE ;

SCHURR, PE .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (12) :1672-1674

[7] THE SYNTHESIS AND CHEMISTRY OF FUNCTIONALIZED FUROCHROMONES .2. THE SYNTHESIS, SOMMELET-HAUSER REARRANGEMENT, AND CONVERSION OF 4,9-DIMETHOXY-7-[(METHYLTHIO)METHYL]-5H-FURO[3,2-G][1]BENZOPYRAN-5-ONETO AMMIOL [J].

GAMMILL, RB .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5035-5041

[8] ANTIATHEROSCLEROTIC AGENTS - A STRUCTURALLY NOVEL BIVALENT INHIBITOR OF ACYLCOA-CHOLESTEROL O-ACYLTRANSFERASE WITH SYSTEMIC ACTIVITY [J].

GAMMILL, RB ;

BELL, FP ;

BELL, LT ;

BISAHA, SN ;

WILSON, GJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (10) :2685-2686

[9] CATALYTIC OSMYLATION AND OXYPALLADATION OF KHELLIN - 2 USEFUL METHODS FOR FURAN RING DEGRADATION - REPLACEMENT OF THE FURAN RING BY AN ISOXAZOLE RING [J].

GAMMILL, RB ;

NASH, SA .

TETRAHEDRON LETTERS, 1984, 25 (28) :2953-2956

[10]

GAMMILL RB, 1983, TETRAHEDRON LETT, V24, P3438