Metal-free POCl3 promoted stereoselective hydrochlorination of ethynylated azaheterocycles

文献情報

出版日 2019-05-29

DOI 10.1039/C9OB00841A

インパクトファクター 3.876

著者

Radhey M. Singh

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要旨

An efficient hydrochlorination of ethynylated azaheterocycles was achieved using POCl3 as a chlorinating agent under metal-free reaction conditions. Mechanistic studies show that the reaction proceeded via nucleophilic attack of POCl3 on the nitrogen of the quinoline ring in a stereoselective manner. The resulting products were versatile intermediates in organic synthesis and were used in the cross-coupling reaction and metal-free synthesis of heterocycles. The developed protocol features inexpensive and easily synthesizable starting materials, easy operation, and high efficiency with a high yield of products.

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.

Metal-free POCl3 promoted stereoselective hydrochlorination of ethynylated azaheterocycles

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