361479-94-9Relevant articles and documents
One-pot multistep Bohlmann-Rahtz heteroannulation reactions: Synthesis of dimethyl sulfomycinamate
Bagley, Mark C.,Chapaneri, Krishna,Dale, James W.,Xiong, Xin,Bower, Justin
, p. 1389 - 1399 (2007/10/03)
(Chemical Equation Presented) The synthesis of dimethyl sulfomycinamate, the acidic methanolysis product of the sulfomycin family of thiopeptide antibiotics, from methyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is achieved in a 2,3,6-trisubstituted pyridine synthesis that proceeds with total regiocontrol in 13 steps by the Bohlmann-Rahtz heteroannulation of a 1-(oxazol-4-yl)enamine or in 12 steps and 9% yield by three-component cyclocondensation with N-[3-oxo-3-(oxazol-4-yl)propanoyl]serine and ammonia in ethanol.
New N-halosuccinimide-mediated reactions for the synthesis of pyridines
Bagley, Mark C.,Glover, Christian,Merritt, Eleanor A.,Xiong, Xin
, p. 811 - 814 (2007/10/03)
5-Bromo-2,6-dialkylpyridine-4-carboxylates are generated in excellent yield by the Michael addition of enaminoesters and ethynyl ketones followed by bromocyclization using N-bromosuccinimide within 1 hour at 0°C. Treatment of the same aminopentadienone intermediates with N-iodosuccinimide facilitates a low temperature cyclodehydration under very mild conditions to give 2,3,6-trisubstituted pyridines with total regiocontrol.
A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines
Bagley, Mark C.,Dale, James W.,Bower, Justin
, p. 1682 - 1683 (2007/10/03)
The one-pot three-component condensation of a β-ketoester, ammonia and an alkynone in the presence of a Bronsted or Lewis acid or Amberlyst 15 ion exchange resin provided 2,3,6-trisubstituted or 2,3,4,6-tetrasubstituted pyridines directly in good yield and with total regiocontrol.