76877-59-3Relevant articles and documents
ALKYLATION OF 3-ETHOXY-2-LITHIOACRYLONITRILE: SYNTHESIS OF 5-ALKYLCYTOSINES
Smirnow, David,Hopkins, Paul B.
, p. 1187 - 1194 (2007/10/02)
The utility of commercially available, inexpensive 3-ethoxyacrylonitrile (1) as a precursor for the synthesis of 5-alkylcytosines was investigated.Metalation of 1 affords a 2-lithio derivative of sufficient stability to allow alkylation with allylic or benzylic bromides and primary iodides which are unbranched at the β-position.The alkylated derivatives are converted to 5-alkylcytosines in modest yield by exposure to sodium ethoxide and urea in ethanol.