TY - JOUR
T1 - Solvent-specific C - N bond formation
T2 - Synthesis of Novel ninhydrin-creatinine heterocyclic condensation products
AU - Penthala, Narsimha Reddy
AU - Yerramreddy, Thirupathi Reddy
AU - Parkin, Sean
AU - Crooks, Peter A.
PY - 2013/2
Y1 - 2013/2
N2 - 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-1H-imidazol-5-yl)-2-hydroxy-1H-ind-ene-1, 3(2H)-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.
AB - 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-1H-imidazol-5-yl)-2-hydroxy-1H-ind-ene-1, 3(2H)-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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U2 - 10.1002/jhet.1107
DO - 10.1002/jhet.1107
M3 - Article
AN - SCOPUS:84876914334
SN - 0022-152X
VL - 50
SP - E156-E159
JO - Journal of Heterocyclic Chemistry
JF - Journal of Heterocyclic Chemistry
IS - SUPPL.1
ER -