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Design and synthesis of a novel intercalating isoxazolyl bis‐lexitropsin conjugate
Author(s) -
Han Xiaochun,
Natale Nicholas R.
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380216
Subject(s) - chemistry , dimethyl acetylenedicarboxylate , nitrile , isoxazole , yield (engineering) , conjugate , anthracene , medicinal chemistry , molar ratio , oxide , organic chemistry , cycloaddition , catalysis , mathematical analysis , materials science , mathematics , metallurgy
9‐Anthracene nitrile oxide directly generated from 9‐anthracenealdoxime and N ‐chlorosuccinamide (NCS), reacts with dimethyl acetylenedicarboxylate (DMAD) and affords the corresponding 3‐(9′‐anthra‐cenyl)‐isoxazole‐4,5‐dicarboxylic acid ester ( 3 ) with good yield in a very short period. Double activation reaction between ( 3 ) and hydrogenated lexitropsin ( 5 ) in a 1:2 molar ratio, produced a bis‐lexitropsin product ( 6 ) (major product) and mono‐lexitropsin product ( 7 ).