ORGANOLEAD-MEDIATED ARYLATION OF ALLYL BETA-KETO-ESTERS - SELECTIVE SYNTHESIS OF 2'-HYDROXYISOFLAVONES

被引：10

作者：

DONNELLY, DMX ^{[1
]}

FINET, JP ^{[1
]}

RATTIGAN, BA ^{[1
]}

机构：

[1] UNIV AIX MARSEILLE 1,CTR ST JEROME,LAB SREP RADICAUX LIBRES & SYNTH,,CNRS,URA 1412,F-13397 MARSEILLE 20,FRANCE

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 13期

关键词：

D O I：

10.1039/p19950001679

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Arylation of the A-ring-unsubstituted and -substituted 3-(alloxycarbonyl)chroman-4-ones 6-8 with [4,5-dimethoxy-2-(methoxymethoxy)phenyl]lead(IV) triacetate 5 followed by selective catalytic deallyloxy-carbonylation-dehydrogenation afforded 2'-protected isoflavones in high overall yields. Acid-catalysed removal of the methoxymethyl group led to the corresponding 2'-hydroxyisoflavones.

引用

页码：1679 / 1683

页数：5

共 32 条

[1] ARYLOXYMETHYL RADICAL CYCLIZATIONS MIMICKING BIOLOGICAL C-C BOND FORMATION TO METHOXY GROUPS
AHMADJUNAN, SA
WALKINGTON, AJ
WHITING, DA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (18): : 2313 - 2320
[2] ASSUMPCAO RM, 1973, PHYTOCHEMISTRY, V12, P1188, DOI 10.1016/0031-9422(73)85049-6
[3] APPLICATION OF ARYLLEAD(IV) DERIVATIVES TO THE PREPARATION OF 3-ARYL-4-HYDROXY-1-BENZOPYRAN-2-ONES
BARTON, DHR
DONNELLY, DMX
FINET, JP
GUIRY, PJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (11): : 1365 - 1375
[4] A FACILE SYNTHESIS OF 3-ARYL-4-HYDROXYCOUMARINS
BARTON, DHR
DONNELLY, DMX
FINET, JP
GUIRY, PJ
[J]. TETRAHEDRON LETTERS, 1989, 30 (12) : 1539 - 1542
[5] SYNTHESIS AND INVITRO EVALUATION OF 2,3-DIMETHOXY-5-(FLUOROALKYL)-SUBSTITUTED BENZAMIDES - HIGH-AFFINITY LIGANDS FOR CNS DOPAMINE-D2 RECEPTORS
BISHOP, JE
MATHIS, CA
GERDES, JM
WHITNEY, JM
EATON, AM
MAILMAN, RB
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (05) : 1612 - 1624
[6] A NEW APPROACH TO SYNTHESIS OF ROTENOIDS - SYNTHESIS OF DEHYDROMUNDUSERONE AND DEHYDROELLIPTONE
CHANDRAS.V
KRISHNAM.M
SESHADRI, TR
[J]. TETRAHEDRON, 1967, 23 (05) : 2505 - &
[7] NEW SYNTHESIS OF ROTENOIDS - APPLICATION TO 9-DEMETHYLMUNDUSERONE, MUNDESERONE, ROTENONIC ACID, DALPANOL, AND ROTENONE
CROMBIE, L
FREEMAN, PW
WHITING, DA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (12): : 1277 - 1285
[8] Dewick P. M., 1994, FLAVONOIDS ADV RES 1, P117
[9] ARYLLEAD TRIACETATES AS SYNTHONS FOR THE SYNTHESIS OF BIFLAVONOIDS .1. SYNTHESIS AND REACTIVITY OF A FLAVANONYLLEAD TRIACETATE
DONNELLY, DMX
FITZPATRICK, BM
FINET, JP
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (13): : 1791 - 1795
[10] A NEW APPROACH TO NEOFLAVONOID SYNTHESIS
DONNELLY, DMX
FINET, JP
GUIRY, PJ
HUTCHINSON, RM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (10): : 2851 - 2852

← 1 2 3 4 →