含杂环烯烃的分子内共轭加成反应

Intramolecular Conjugate Additions with Heterocyclic Olefins.

作者信息

Boblak Kenneth N, Gasonoo Makafui, Zhang Yiliang, Klumpp Douglas A

机构信息

Department of Chemistry and Biochemistry, Northern Illinois University , DeKalb, Illinois 60115, United States.

出版信息

J Org Chem. 2015 Dec 18;80(24):11948-52. doi: 10.1021/acs.joc.5b01701. Epub 2015 Nov 23.

DOI:10.1021/acs.joc.5b01701

PMID:26569433

Abstract

The intramolecular reactions of olefinic N-heterocycles have been studied. In triflic acid-promoted reactions, conjugate addition is observed with pyrazine-, 2-pyrimidine-, and 2-quinoxaline-based olefins and a phenyl group nucleophile. Markovnikov addition is observed with pyridine and 5-quinoxaline-based olefins. These results are in accordance with previous observations relating the type of addition-conjugate or Markovnikov-to the positions of olefinic substituents of the N-heterocycle.

摘要

已对烯烃类氮杂环的分子内反应进行了研究。在三氟甲磺酸促进的反应中，观察到吡嗪基、2 -嘧啶基和2 -喹喔啉基烯烃与苯基亲核试剂发生共轭加成。观察到吡啶基和5 -喹喔啉基烯烃发生马氏加成。这些结果与先前关于加成类型（共轭或马氏）与氮杂环烯烃取代基位置关系的观察结果一致。