Double dearomatization of bis(diphenylphosphinamides) through anionic cyclization. A facile route of accessing multifunctional systems with antitumor properties.
The sequential one-pot double dearomatization of bis(N-benzyl-P,P-diphenylphosphinamides) via anionic cyclization is described for the first time. Protonation and alkylation of the dearomatized dianions provide bis(tetrahydro-2,1-benzazaphospholes) in good yield and with very high regio- and stereocontrol. Acid-catalyzed methanolysis of the bisheterocycles affords bis(methyl gamma-aminophosphinates) stereospecifically. The doubly phosphorylated systems proved to be active against a series of cancer cell lines.
Ruiz-Gómez
Gloria
G
Area de Química Orgánica, Universidad de Almería, Carretera de Sacramento, 04120 Almería, Spain.
Iglesias
María José
MJ
Serrano-Ruiz
Manuel
M
García-Granda
Santiago
S
Francesch
Andrés
A
López-Ortiz
Fernando
F
Cuevas
Carmen
C
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D000838:Anions / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D001372:Aza Compounds / Q000737:chemistry; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003500:Cyclization; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000577:Amides; D000838:Anions; D000970:Antineoplastic Agents; D001372:Aza Compounds; D010720:Phosphines