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One‐Step Synthesis of Lumazine and Xanthine: First Co‐Crystal of Lumazine and Perchloric Acid with a Unique Monohydrated Hydronium Ion (H 5 O 2 + ) Mediated Supramolecular Assembly of the Lumazine Dimer
Author(s) -
Goswami Shyamaprosad,
Maity Annada C.,
Fun HoongKun
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700271
Subject(s) - chemistry , perchloric acid , protonation , hydrogen bond , xanthine , supramolecular chemistry , stereochemistry , crystal structure , crystallography , organic chemistry , ion , molecule , enzyme
A perchloric acid mediated one‐step synthesis of lumazine derivatives from pterins and xanthine from guanine is reported. However, 2‐pivaloylamino derivatives of pterins underwent simple hydrolysis of the pivaloylamino group generating free pterin compounds, but the 2‐oxo derivatives, that is, the lumazine compounds, were not obtained. A novel supramolecular assembly is constructed by the unique hydrogen bonding of H 5 O 2 + bridging two hydrogen‐bonded dimers of lumazine to form the co‐crystal 21 with aqueous perchloric acid. In contrast, N 2 ‐pivaloyl‐6‐bromo‐5‐deazapterin was simply hydrolysed to form the protonated deazapterin 22 , which forms a unique six‐membered cyclic hydrogen‐bonded structure leading to the generation of a polymeric supramolecular assembly. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)