Ionic liquid phase organic synthesis (IoLiPOS) methodology applied to the preparation of new 3,4-dihydropyrimidine-2(1H)-ones bearing bioisostere group in N-3 position

Add time:07/21/2019    Source:sciencedirect.com

The ionic liquid phase organic synthesis (IoLiPOS) methodology has been used for the preparation of new 3,4-dihydropyrimidine-2(1H)-ones (DHPMs) bearing bioisostere group in N-3 position. For the 3,4-DHPMs substituted with various thiazole rings, the strategy involved a three-component Biginelli condensation in the second step with good yields (93–96%) from ILP bound acetoacetate, aromatic aldehyde (93–97% yield), and N-methyl urea followed by N-3 alkylation with chloroacetonitrile on the ILP bound 3,4-DHPM. Quantitative thionation of the nitrile group grafted on the ILP bound 3,4-DHPM was realized in MeOH with a 40–48% solution of ammonium sulfide and subsequent addition of α-bromoketone produced the thiazole ring appended on the 3,4-DHPM core. After cleavage by transesterification, the target compounds were obtained in good overall yields (47–50%). The efficiency of the IoLiPOS methodology was also demonstrated by the preparation of new 3,4-DHPMs with a tetrazole ring in N-3 position in 5 steps (53–61% overall yield) via the ILP bound 3-cyanomethyl 3,4-DHPM as key intermediate.

We also recommend Trading Suppliers and Manufacturers of ETHYL 2-[3-(2-AMINO-2-THIOXOETHYL)-4-OXO-3,4-DIHYDROPHTHALAZIN-1-YL]ACETATE (cas 131666-72-3). Pls Click Website Link as below: cas 131666-72-3 suppliers

Prev:Occurrence of autoimmune antibodies to liver microsomal proteins associated with lethal hepatitis in LEC rats: effects of TJN-101 ((+)-(6S,7S,R-biar)-5,6,7,8-tetrahydro-1,2,3,12-tetramethoxy-6,7-dimethyl-10,11-methylenedioxy-6-dibenzo[a,c]cyclooctenol) on the development of hepatitis and the autoantibodies
Next:Synthesis of novel lupane triterpenoid-indazolone hybrids with oxime ester linkage)