Design and effective synthesis of the first 4-aza-2,3-didehydropodophyllotoxin rigid aminologue: a N-methyl-4-[(3,4,5-trimethoxyphenyl)amino)]-1,2-dihydroquinoline-lactone.
The first N1-alkyl-4-amino-1,2-dihydroquinoline-lactone has been prepared by a five-step sequence in a 51% overall yield via the corresponding furo[3,4-b]quinolin-1(3H)-one. A new practical synthesis of this intermediate was carried out using versatile, commercially available starting materials and constitutes the shortest and highest yielding route. These synthetic pathways could be widened with a view toward the preparation of different substituted derivatives, which could be considered as rigid aminologues of 4-aza-2,3-didehydropodophyllotoxins.
Labruère
Raphaël
R
Laboratoire de Chimie Thérapeutique, UMR CNRS No. 8638, Université Paris Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4 avenue de l'Observatoire, 75270 Paris Cedex 06, France.
Helissey
Philippe
P
Desbène-Finck
Stéphanie
S
Giorgi-Renault
Sylviane
S
D000586:Amination; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011034:Podophyllotoxin / Q000138:chemical synthesis* / Q000737:chemistry
C529507:4-methyl-6,7-(methylenedioxy)-9-((3,4,5-trimethoxyphenyl)amino)-3a,4-dihydrofuro(3.4-b)quinolin-1(3H)-one; D001372:Aza Compounds; D006576:Heterocyclic Compounds, 4 or More Rings; D007783:Lactones; D006859:Hydrogen; D011034:Podophyllotoxin