Divergent synthesis of 3,4-dihydro-2H-benzo[h]chromen-2-one and fluorenone derivatives from ortho-alkynylarylketones

文献情報

出版日 2023-10-25

DOI 10.1039/D3OB01492D

インパクトファクター 3.876

著者

Jantra Jantrapirom, Nitwaree Palavong

原文を見る

要旨

Our research has led to the development of a divergent synthesis approach for the synthesis of 3,4-dihydro-2H-benzo[h]chromen-2-one 3 and fluorenone 9 derivatives using ortho-alkynylarylketones as common precursors. The synthesis of 3,4-dihydro-2H-benzo[h]chromen-2-ones 3 employed silver catalyzed ketonization to form polycarbonyl intermediates which underwent double intramolecular cyclization and decarboxylation to generate a lactone and a phenyl ring in a one-pot fashion. In addition, the same precursor could be used to prepare fluorenone derivatives 9 under acidic conditions. The reaction proceeded via the formation of indenone analogs, followed by the generation of the para-quinone methide intermediate and intramolecular cyclization to provide the corresponding products in good yields.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.