25475-67-6Relevant articles and documents
On Pyridopyrazinol Chemistry: Synthesis of Chemiluminescent Substances
Gagnot, Glwadys,Legrand, Pierre,Tadros, Amira,Ezzahra Hibti, Fatima,Quatela, Alessia,Janin, Yves L.
, p. 2477 - 2484 (2021)
Our work on new chemiluminescent substances related to the marine luciferin coelenterazine (λ max= 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 (λ max= 546 and 462 nm).
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Sanders et al.
, p. 4717 (1972)
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New fluorescent isoquinoline derivatives
Balog, József,Riedl, Zsuzsanna,Hajós, Gy?rgy,Miskolczy, Zsombor,Biczók, László
body text, p. 5264 - 5266 (2011/10/19)
Various structural modifications of 3-amino and 3-hydroxyisoquinolines have been carried out to provide new fluorescent derivatives. The transformations involved nucleophilic substitution of a bromine atom or a triflate moiety at positions 1 and 3, respectively, as well as the condensation reaction of a 3-amino group with triethyl orthoformate and subsequent transformation with amines to give amidines. The new compounds have been studied by fluorescence spectroscopy.
A general approach to 3-aminoisoquinoline, its N-mono and N,N-disubstituted derivatives
Zdrojewski,Jonczyk
, p. 12439 - 12444 (2007/10/02)
Condensation of 2-cyanomethyl benzaldehydes 1 with 2 (ammonia, primary or secondary amines) carried out in the presence of a catalytic amount of trifluoroacetic acid, afforded 3-aminoisoquinolines 3. In the case of primary amines azomethines 4 were formed at first; they dissociated and subsequently yielded 3 in a rather slow process.