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New Heterocycles from the Reaction between Some Natural α‐Amino Acid Hydrazides and Formaldehyde
Author(s) -
Verardo Giancarlo,
Toniutti Nicoletta,
Gorassini Andrea,
Giumanini Angelo G.
Publication year - 1999
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/(sici)1099-0690(199911)1999:11<2943::aid-ejoc2943>3.0.co;2-x
Subject(s) - chemistry , phenylhydrazine , formaldehyde , pyridine , ring (chemistry) , condensation reaction , aqueous solution , medicinal chemistry , organic chemistry , tryptophan , chirality (physics) , amino acid , stereochemistry , catalysis , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
The ring forming condensation between some natural α‐amino acid phenylhydrazides ( 1 ) and aqueous formaldehyde ( 2 ) has opened a novel synthetic route to hexahydro‐1,2,4‐triazin‐6‐one derivatives ( 3 ). Polycyclic systems were obtained from the same reaction carried out with L ‐aspartic acid 1,4‐bis(2‐phenylhydrazide) ( 1d ), L ‐histidine phenylhydrazide ( 1e ) and L ‐tryptophan phenylhydrazide ( 1f ) which gave perhydro‐4,6‐dioxo‐2,8‐diphenyl[1,2,4]triazino[4,5‐ d ][1,2,4]triazepine ( 5 ) perhydro‐1‐oxo‐3‐phenylimidazo[5,4‐ d ][1,2,4]triazino[4,5‐ a ]pyridine ( 7 ) and 1,2,3‐ H ‐3‐(2‐phenylcarbazoyl)‐β‐carboline ( 8 ), respectively. Substrates 1 were conveniently obtained by direct reaction of phenylhydrazine with L ‐α‐amino acid esters retaining the original chirality.