Synthesis of phosphaisoquinolin-1-ones by Pd(II)-catalyzed cyclization of o-(1-alkynyl)phenylphosphonamide monoesters.
A Pd(II)-catalyzed intramolecular cyclization of o-(1-alkynyl)phenylphosphonamide monoethyl esters was examined, and a new class of six-membered phosphorus heterocycles (phosphaisoquinolin-1-ones) were formed with high regioselectivity and good yields. The present reaction is the first example of intramolecular addition of P-NH to substituted alkynes, which provides a valuable way to synthesize novel phosphorus heterocycles with potential bioactivities.
Tang
Wei
W
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Ding
Yi-Xiang
YX
D000577:Amides / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D003500:Cyclization; D004354:Drug Screening Assays, Antitumor; D004952:Esters / Q000737:chemistry*; D007546:Isoquinolines / Q000737:chemistry*; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry* / Q000494:pharmacology; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D000970:Antineoplastic Agents; D004952:Esters; D007546:Isoquinolines; D063065:Organophosphonates; D010165:Palladium