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Synthesis 2019; 51(06): 1377-1382
DOI: 10.1055/s-0037-1610670
DOI: 10.1055/s-0037-1610670
paper
Synthesis of Novel Isoquinolino[5,4-ab]phenanthridine Derivatives via Pictet–Spengler Reaction
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 (online)
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.
Key words
homophthalimide - isoquinoline-1,3-dione - naphthalimide - phenanthridine - Pictet–Spengler reaction - Suzuki–Miyaura cross-coupling reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610670. Spectra of the new compounds are included.
- Supporting Information
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