Expedient synthesis of mequitazine an antihistaminic drug by palladium catalyzed allylic alkylation of sodium phenothiazinate.
A short and straightforward synthesis of the antihistaminic drug mequitazine is reported, based on an efficient palladium catalyzed allylic alkylation of 1-aza-bicyclo[2.2.2]oct-2-en-3-ylmethyl acetate using sodium phenothiazinate in mild conditions.
Gonnot
Vanessa
V
Faculty of Pharmacy, University of Strasbourg, CNRS-UMR 7199, 74 route du Rhin, 67401 Illkirch, France.
Nicolas
Marc
M
Mioskowski
Charles
C
Baati
Rachid
R
D000478:Alkylation; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D006634:Histamine H1 Antagonists / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010640:Phenothiazines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013843:Thiazines / Q000737:chemistry*
C546254:1-aza-bicyclo(2.2.2)oct-2-en-3-ylmethyl acetate; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006634:Histamine H1 Antagonists; D009942:Organometallic Compounds; D010640:Phenothiazines; D013843:Thiazines; C546253:sodium phenothiazinate; D010165:Palladium; C006069:mequitazine