TY - JOUR
T1 - Highly regioselective nucleophilic/cycloaddition reactions of W-arylamino l,3-diazabuta-l,3-dienes with a-nitrosostyrenes
T2 - Synthesis of functionalised imidazoles, and imidazole oxides
AU - Sharma, Arun
AU - Hundal, Geeta
AU - Obrai, Sangeeta
AU - Mahajan, Mohinder P.
PY - 1999
Y1 - 1999
N2 - The a-nitrosostyrenes 2, generated in situ from a-halogeno oximes, underwent regioselective cycloadditon/ nucleophilic reactions with W-arylamino l,3-diazabuta-l,3-dienes 1 leading to a mixture of imidazoles, and cyclic nitrones shown to have structures 3, and 4, respectively, by X-ray crystallographic analysis. The structure 4 for cyclic nitrones was also supported by their 1,3-dipolar cycloaddition with dimethyl acetylenedicarboxylate (DM AD). The thermolysis of nitrones 4 gives imidazoles 3 via oxadiazine intermediates 6.
AB - The a-nitrosostyrenes 2, generated in situ from a-halogeno oximes, underwent regioselective cycloadditon/ nucleophilic reactions with W-arylamino l,3-diazabuta-l,3-dienes 1 leading to a mixture of imidazoles, and cyclic nitrones shown to have structures 3, and 4, respectively, by X-ray crystallographic analysis. The structure 4 for cyclic nitrones was also supported by their 1,3-dipolar cycloaddition with dimethyl acetylenedicarboxylate (DM AD). The thermolysis of nitrones 4 gives imidazoles 3 via oxadiazine intermediates 6.
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U2 - 10.1039/a808574i
DO - 10.1039/a808574i
M3 - Article
AN - SCOPUS:0007892384
SN - 0300-922X
SP - 615
EP - 619
JO - Journal of the Chemical Society - Perkin Transactions 1
JF - Journal of the Chemical Society - Perkin Transactions 1
IS - 5
ER -