Syntheses of 6,7-Benzotropolones by a Sequence of Acylation (or α-Hydroxyalkylation/Oxidation), Ring-Closing Metathesis, and Hydrolysis/β-Elimination

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2022-11-01 DOI:10.1021/acs.joc.2c01968

Sarah N. Momm, and , Reinhard Brückner*,

引用次数: 1

Abstract

Starting from ortho-bromostyrenes, 12 6,7-benzotropolones were synthesized in 3 or 4 steps. Br/Li exchanges provided the respective ortho-lithiostyrenes. The latter were acylated by a Weinreb amide, if unhindered, or hydroxyalkylated by an aldehyde, if hindered (an oxidation ensuing thereafter). Acetonide-containing benzannulated nonatrienones resulted. Ring-closing olefin metatheses converted them into acetonide-containing benzocycloheptadienones. Treatment with aq. HCl caused hydrolyses followed by β-elimination reactions giving 6,7-benzotropolones.

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通过酰化(或α-羟基烷基化/氧化)、合环复分解和水解/β-消除合成6,7-苯并唑波酮

以邻溴苯乙烯为起始原料，经3、4步合成了12个6,7-苯并唑波酮类化合物。Br/Li交换体提供了各自的邻苯乙烯。后者被Weinreb酰胺酰基化，如果阻碍，或被醛羟基烷基化(随后的氧化)。得到含苯并环的非三烯酮。闭环烯烃的转化反应将它们转化为含乙酰胺的苯并环庚二烯酮。用aq. HCl处理引起水解，随后发生β-消除反应，得到6,7-苯并唑波酮。

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.