Preparation of methylfuro[3,4-b][1,4]benzodioxinones as intermediates for the synthesis of substituted polycyclic systems.: Importance of the acid used as catalyst

被引：11

作者：

Bozzo, C ^{[1
]}

Pujol, MD ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, Quim Farmaceut Lab, E-08028 Barcelona, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 40期

关键词：

lactonization; benzodioxins; polycyclic heterocyclic compounds;

D O I：

10.1016/S0040-4020(99)00670-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lactones 10 and 11 were conveniently prepared in excellent yield by reaction of the corresponding gamma-hydroxy amides 6, 7 and 8 in the presence of propionic acid in catalytic amounts. By increasing the ratio of propionic acid used, under the same reaction conditions, the hydroxy amide 6 reacted to give a mixture of ketoamides 13 (cis / trans). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：11843 / 11852

页数：10

共 22 条

[1] THE CYCLISATION OF OLEFINIC ACIDS TO KETONES AND LACTONES [J].

ANSELL, MF ;

PALMER, MH .

QUARTERLY REVIEWS, 1964, 18 (02) :211-225

[2] DIRECTED LITHIATION OF TERTIARY BETA-AMINO BENZAMIDES [J].

COMINS, DL ;

BROWN, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3566-3572

[3] ACYLATION OF ORGANOLITHIUM REAGENTS BY ESTERS IN THE PRESENCE OF CHLOROTRIMETHYLSILANE [J].

COOKE, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (06) :951-953

[4] KINETIC RESOLUTION OF LACTONES BY ENANTIOSELECTIVE PROTONATION OF THE CORRESPONDING CARBOXYLATE WITH A CHIRAL ACID [J].

FUJI, K ;

NODE, M ;

MURATA, M ;

TERADA, S ;

HASHIMOTO, K .

TETRAHEDRON LETTERS, 1986, 27 (44) :5381-5382

[5] ENANTIOSELECTIVE LACTONIZATION OF SODIUM 4-HYDROXYPIMELATE UNDER ABIOLOGICAL CONDITIONS [J].

FUJI, K ;

NODE, M ;

TERADA, S ;

MURATA, M ;

NAGASAWA, H ;

TAGA, T ;

MACHIDA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (22) :6404-6406

[6] NOVEL SYNTHESIS OF (+/-)-VERMICULINE [J].

FUKUYAMA, Y ;

KIRKEMO, CL ;

WHITE, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (02) :646-647

[7]

GALLI C, 1978, ORG SYNTH, V58, P98

[8]

GUILLAUMET G, 1994, Patent No. 624582

[9]

GUILLAUMET G, 1979, TETRAHEDRON LETT, V45, P4379

[10] Novel selective PDE IV inhibitors as antiasthmatic agents. Synthesis and biological activities of a series of 1-aryl-2,3-bis(hydroxymethyl)naphthalene lignans [J].

Iwasaki, T ;

Kondo, K ;

Kuroda, T ;

Moritani, Y ;

Yamagata, S ;

Sugiura, M ;

Kikkawa, H ;

Kaminuma, O ;

Ikezawa, K .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (14) :2696-2704

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