S. Nayak, Vikramdeep Monga, N. Kaur
Nov 1, 2007
Citations
0
Influential Citations
2
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
Two diverse methodologies describe the first synthesis of suitably protected N-α,N-1(τ)-dialkyl-Lhistidine derivatives. Synthesis of suitably protected N-α,N-1(τ)-dialkyl-L-histidines 7-9 containing different alkyl groups at the N-α and N-1(τ) positions was achieved in four steps starting from L-histidine methyl ester. Whereas, in the one-step alternate route N-α-Boc-L-histidine methyl ester upon direct and simultaneous N-α and N-1(τ) alkylation with various alkyl halides in the presence of sodium hydride in DMF easily afforded N-α,N-1(τ)-dialkyl-L-histidines 14 containing identical alkyl group at the N-α and N-1(τ) positions in high yields. Both procedures allowed facile entry to methyl and other higher alkyl groups at the N-α-position of the histidine ring