Phosphine-catalyzed [4 + 2] annulation of γ-benzyl allenoates: facile synthesis of benzothieno[3,2-b]pyran derivatives

文献信息

发布日期 2018-03-27

DOI 10.1039/C8OB00004B

影响因子 3.876

作者

Shanshan Ma, Aimin Yu, Xiangtai Meng

查看原文

摘要

An efficient tris(4-methoxyphenyl)phosphine-catalyzed domino reaction between γ-benzyl allenoates and ethyl (Z)-2-(3-oxobenzo[b]thiophen-2(3H)-ylidene)acetate has been developed, which produces a series of 2H-benzo[4,5]thieno[3,2-b]pyran derivatives in high yields. The substrate scope includes both electron-withdrawing (e.g., halogen) and electron-donating (e.g., methoxy) groups on both the benzothiophene and allenoate moieties. The reaction can also be performed on the gram scale with good yield (e.g., 77%). In this reaction, γ-substituted allenoate acts as a two-carbon synthon, in a manner rarely reported in the literature to date.

期刊推荐

Organic Geochemistry

Drug and Chemical Toxicology

Bioorganic Chemistry

Applied Clay Science

Journal of Natural Products

Bulletin of Materials Science

Journal of Dispersion Science and Technology

Applied Surface Science

European Journal of Medicinal Chemistry

Annual Review of Public Health

来源期刊

Organic & Biomolecular Chemistry

CiteScore: 3.4

自引率: 10.3%

年发文量: 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.