MICHAEL ADDITIONS IN ANHYDROUS MEDIA - NOVEL SYNTHESIS OF OXYGENATED COUMARINS

被引：42

作者：

KRAUS, GA

PEZZANITE, JO

机构：

[1] Department of Chemistry, Iowa State University, Ames, Iowa

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 14期

关键词：

D O I：

10.1021/jo01328a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general procedure is described where an aryllithium, generated by metalation of a protected phenol with n-butyllithium, adds in a conjugate manner to diethyl ethoxymethylenemalonate to give after acid hydrolysis an oxygenated 3-carbethoxycoumarin. By this procedure the ethyl vinyl ethers 9, 11, 13, and 15 are converted into the corresponding coumarins 10, 12, 14, and IS in a single reaction vessel in good yield. © 1979, American Chemical Society. All rights reserved.

引用

页码：2480 / 2482

页数：3

共 15 条

[1] RELATIONSHIP BETWEEN STRUCTURE AND ANTICOAGULANT ACTIVITY OF COUMARIN DERIVATIVES
ARORA, RB
MATHUR, CN
[J]. BRITISH JOURNAL OF PHARMACOLOGY AND CHEMOTHERAPY, 1963, 20 (01): : 29 - &
[2] Boehm T., 1931, ARCH PHARM, V269, P25
[3] CHAKRABORTY DP, 1957, ANN BIOCHEM EXP MED, V17, P57
[4] Ellis G. P., 1974, PROG MED CHEM, V10, P109
[5] The alkylation of hydroxynaphthoquinone II Carbon alkylation
Fieser, LF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1926, 48 : 3201 - 3214
[6] Dibenzofuran XVIII Isomeric metalation products of some phenols and their methyl ethers
Gilman, H
Willis, HB
Cook, TH
Webb, FJ
Meals, RN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 : 667 - 669
[7] ORGANIC PHOTOCHEMISTRY .12. FURTHER STUDIES ON MECHANISM OF COUMARIN PHOTODIMERIZATION - OBSERVATION OF AN UNUSUAL HEAVY ATOM EFFECT
HOFFMAN, R
WELLS, P
MORRISON, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (01) : 102 - &
[8] Kadis S., 1972, MICROB TOXINS, V7
[9] LINK KP, 1943, HARVEY LECT, V39, P162
[10] Molho D., 1965, U.S. Patent, Patent No. 3175943

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