76595-31-8Relevant academic research and scientific papers
Remarkable Chichibabin-type cyclotrimerisation of 3-nitrotyrosine, tyrosine and phenylalanine to 3,5-diphenylpyridine derivatives induced by hypochlorous acid
Panzella,Di Donato,Comes,Napolitano,Palumbo,D'Ischia
, p. 6457 - 6460 (2005)
Reaction of 3-nitrotyrosine with HOCl in aqueous phosphate buffer (pH 7.4) leads to a mixture of extractable products, including 3,5-di(4-hydroxy-3- nitrophenyl)pyridine (15% isolated yield) and 3,5-di(4-hydroxy-3-nitrophenyl)-2- (4-hydroxy-3-nitrophenylmethyl)pyridine (3%) arising by a Chichibabin-like pyridine synthesis via N-chloroimine intermediates. Under the same conditions, phenylalanine gives 3,5-diphenylpyridine in 9% isolated yield, while tyrosine leads to 3,5-di(4-hydroxyphenyl)pyridine (3%) and 3-(3-chloro-4-hydroxyphenyl)- 5-(4-hydroxyphenyl)pyridine (3%).
Facile one-pot synthesis of tetrahydroisoquinolines from amino acids via hypochlorite-mediated decarboxylation and Pictet-Spengler condensation
Maresh, Justin J.,Crowe, Sean O.,Ralko, Arthur A.,Aparece, Mark D.,Murphy, Casey M.,Krzeszowiec, Mark,Mullowney, Michael W.
, p. 5047 - 5051 (2015/01/09)
A convenient method for oxidative decarboxylation of α-amino acids is presented. The aldehyde products may be isolated or converted to tetrahydroisoquinolines by addition of dopamine via Pictet-Spengler reaction. Racemic products are generated by phosphate buffer >300 mM to maximize regioselectivity. (S)-Enantiomer products are generated by norcoclaurine synthase reaction in maleic acid buffer to minimize chemical background reaction.
