Divergent Sc(OTf)3-Catalyzed Tandem Cyclization of o-Hydroxyphenyl Enaminones with 1,3,5-Triazinanes: Access to C3-Aminomethyl Chromones and Tetrahydropyrimidines

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2024-10-08 DOI:10.1002/ajoc.202400391

Siyang Han, Chengcheng Fang, Sifeng Li, Xiaoye Mo, Yingqian Xu, Baigang An, Bin Cheng

引用次数: 0

Abstract

A Sc(OTf)₃-catalyzed tandem cyclization reaction of o-hydroxyphenyl enaminones with 1,3,5-triazinanes has been developed to generate two distinct annulated products in moderate to good yields, which is dominated by the electronic characteristics of the 1,3,5-triazinanes. The 1,3,5-triaryl-1,3,5-triazinane reacted as C−N synthon to produce C3-aminomethyl chromone, while the 1,3,5-trialkyl-1,3,5-triazinane acted as C−N−C−N synthons to deliver N,N-dialkyl tetrahydropyrimidine with a free hydroxyl group.

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.