一种从β-芳基氨基卟啉合成N-芳基喹啉并[2,3,4-at]卟啉的新方法。

A new synthetic approach to N-arylquinolino[2,3,4-at]porphyrins from beta-arylaminoporphyrins.

作者信息

Pereira Ana M V M, Alonso Cristina M A, Neves Maria G P M S, Tomé Augusto C, Silva Artur M S, Paz Filipe A A, Cavaleiro José A S

机构信息

Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.

出版信息

J Org Chem. 2008 Sep 19;73(18):7353-6. doi: 10.1021/jo800975c. Epub 2008 Aug 22.

DOI:10.1021/jo800975c

PMID:18722409

Abstract

A new reaction leading to porphyrins bearing fused rings is described. Novel N-arylquinolino[2,3,4-at]porphyrins 2 were obtained by thermal oxidative cyclization of beta-arylaminoporphyrins 1. The starting beta-arylaminoporphyrins were prepared by two routes: (i) nucleophilic displacement of the nitro group from 2-nitro-5,10,15,20-tetraphenylporphyrin by anilines and (ii) palladium-catalyzed amination of bromobenzene derivatives with (2-amino-5,10,15,20-tetraphenylporphyrinato)nickel(II). The N-arylquinolino[2,3,4-at]porphyrins show interesting UV-vis spectra with strong absorption bands in the red region.

摘要

描述了一种生成带有稠环卟啉的新反应。通过β-芳基氨基卟啉1的热氧化环化反应得到了新型的N-芳基喹啉并[2,3,4-at]卟啉2。起始的β-芳基氨基卟啉通过两条路线制备：(i) 用苯胺将2-硝基-5,10,15,20-四苯基卟啉中的硝基进行亲核取代；(ii) 钯催化溴苯衍生物与(2-氨基-5,10,15,20-四苯基卟啉基)镍(II)进行胺化反应。N-芳基喹啉并[2,3,4-at]卟啉显示出有趣的紫外-可见光谱，在红色区域有强吸收带。