Synthesis 2019; 51(06): 1377-1382
DOI: 10.1055/s-0037-1610670
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel Isoquinolino[5,4-ab]phenanthridine Derivatives via Pictet–Spengler Reaction

Min-Chen Tsai
,
Pei Yu Huang
,
Liang Sheng Syu
,
Tzenge-Lien Shih*
Department of Chemistry, Tamkang University, 25137 Tamsui Dist., New Taipei City, Taiwan, Republic of China   Email: tlshih@mail.tku.edu.tw
› Author Affiliations
The work was supported by the Ministry of Science and Technology (MOST 104-2113-M-032-002) in Taiwan.
Further Information

Publication History

Received: 11 September 2018

Accepted after revision: 16 October 2018

Publication Date:
21 November 2018 (eFirst)

Abstract

The reaction of 5-amino-2-[2-(dimethylamino)ethyl]-6-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione with a series of aldehydes in acidic media (phosphoric acid, trifluoromethanesulfonic acid, and trifluoroacetic acid) is described. This key step is based on the Pictet–Spengler reaction to synthesize ten novel isoquinolino[5,4-ab]phenanthridine derivatives. The most effective acid is phosphoric acid and optimized yields were obtained. The frameworks of target compounds are unique and have never been reported.

Supporting Information

 
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