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Solvent‐Specific C―N Bond Formation: Synthesis of Novel Ninhydrin–Creatinine Heterocyclic Condensation Products
Author(s) -
Penthala Narsimha Reddy,
Yerramreddy Thirupathi Reddy,
Parkin Sean,
Crooks Peter A.
Publication year - 2013
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.1107
Subject(s) - chemistry , ninhydrin , solvent , condensation , acetic acid , benzene , organic chemistry , condensation reaction , ring (chemistry) , sodium acetate , medicinal chemistry , amino acid , catalysis , biochemistry , physics , thermodynamics
Novel ninhydrin–creatinine heterocyclic condensation products ( 3–5 ) were synthesized under different solvent conditions. The compound 2‐(2‐amino‐1‐methyl‐4‐oxo‐4,5‐dihydro‐1 H ‐imidazol‐5‐yl)‐2‐hydroxy‐1 H ‐ind‐ene‐1,3(2 H )‐dione ( 3 ) was formed by reacting ninhydrin ( 1 ) with creatinine ( 2 ) in the presence of sodium acetate in acetic acid. The same reactants afforded the zwitterionic compound 4 when the reaction was carried out in water, and a novel oxadiazine ring system (product 5 ) was generated when benzene was used as solvent.
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