PHOTOLACTAMIZATION - A NOVEL SYNTHETIC ENTRY INTO LARGE RING-SIZED LACTAMS

被引：14

作者：

QUINKERT, G

NESTLER, HP

SCHUMACHER, B

DELGROSSO, M

DURNER, G

BATS, JW

机构：

[1] Institut für Organische Chemie der Universität, D 6000 Frankfurt am Main 50, Niederurseler Hang

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 15期

关键词：

PHOTOLACTAMIZATION; MACROCYCLIC LACTAMS; DIENE KETENES; ORTHO-QUINOL ACETATES;

D O I：

10.1016/0040-4039(92)88118-O

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diene ketenes smoothly accessible by photochemical ring cleavage of omicron-quinol acetates, in the presence of primary or secondary amines afford the corresponding amides. In an intramolecular version of this reaction macrocyclic lactams of type A are produced, if aminoalkylated omicron-quinol acetates of type C are used as photo reactants. These photo reactants are available on acid mediated removal of the Boc-protecting group from Wessely acetoxylation products of type D, easily formed via compounds of type E from aminoalkylated phenols of type F.

引用

页码：1977 / 1980

页数：4

共 3 条

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QUINKERT, G ;

BILLHARDT, UM ;

JAKOB, H ;

FISCHER, G ;

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HEIM, N ;

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[3] ON DIEN-KETENES FROM ORTHO-QUINOL-ACETATES [J].

QUINKERT, G ;

KLEINER, E ;

FREITAG, BJ ;

GLENNEBERG, J ;

BILLHARDT, UM ;

CECH, F ;

SCHMIEDER, KR ;

SCHUDOK, C ;

STEINMETZER, HC ;

BATS, JW ;

ZIMMERMANN, G ;

DURNER, G ;

REHM, D ;

PAULUS, EF .

HELVETICA CHIMICA ACTA, 1986, 69 (03) :469-537

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