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On pyridopyrazinol chemistry, synthesis of chemiluminescent substances

Abstract : Our work on new chemiluminescent substances related to the marine luciferin coelenterazine (λmax = 465 nm) led us to attempt the synthesis of four nitrogen-rich pyridopyrazine-bearing analogues. Accordingly, the preparation of the corresponding benzyl-bearing pyridopyrazinols is studied. By varying the conditions for the condensation of phenylpyruvic acid with 1,2-diaminopyridine or 3,4-diaminopyridine, all the possible pyridopyrazin-2-ol regioisomers are isolated and properly characterized, including by means of crystallographic studies. The ensuing syntheses of the halogenated pyridopyrazines are fraught with difficulties ranging from extensive decomposition to an unexpected ring contraction. In one instance, the inherently reductive mixture of phosphorus oxychloride and phosphorus trichloride provides 2-benzyl-3-chloropyrido[2,3-b]pyrazine. This precursor is then transformed into the target O-acetylated luciferin (6,8-dibenzylimidazo[1,2-a]pyrido[3,2-e]pyrazin-9-yl acetate). The ‘benzo’ derivative of this analogue (i.e., 2,12-dibenzylimidazo[1′,2′:1,6]pyrazino[2,3-c]isoquinolin-3-yl acetate) is also prepared and the chemiluminescence emission spectra of these compounds are determined in a phosphate buffer (λmax = 546 and 462 nm).
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Contributor : Yves Janin Connect in order to contact the contributor
Submitted on : Saturday, March 20, 2021 - 12:18:12 PM
Last modification on : Tuesday, September 13, 2022 - 4:59:32 PM
Long-term archiving on: : Monday, June 21, 2021 - 6:13:49 PM


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Glwadys Gagnot, Pierre Legrand, Amira Tadros, Fatima Ezzahra Hibti, Alessia Quatela, et al.. On pyridopyrazinol chemistry, synthesis of chemiluminescent substances. Synthesis: Journal of Synthetic Organic Chemistry, 2021, 53, ⟨10.1055/a-1396-8607⟩. ⟨pasteur-03175527⟩



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