634603-35-3Relevant academic research and scientific papers
Thermolysis of geminal diazides: Reagent-free synthesis of 3-hydroxypyridines
Erhardt, Hellmuth,Kunz, Kevin A.,Kirsch, Stefan F.
supporting information, p. 178 - 181 (2017/11/27)
An operationally simple protocol for the rapid and efficient construction of highly substituted 3-hydroxypyridines is presented. The thermally induced cyclization of easily constructed geminal diazides derived from β- ketoesters having an additional olefin moiety affords the title compounds in yields up to 97% under reagent-free conditions. The new method allows for the synthesis of preparative quantities of material. Additionally, the synthetic utility of the pyridine products for the synthesis of valuable heterocycles is described.
Multiple pathways in the synthesis of new annelated analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (emivirine)
Therkelsen, Frans D.,Hansen, Anne-Lene L.,Pedersen, Erik B.,Nielsen, Claus
, p. 2908 - 2918 (2007/10/03)
Condensation of 3-(3,5-dimethylphenyl)-2-oxocyclopentanecarboxamide (11) with oxalyl chloride and condensation of ethyl 2-benzylamino-5-methyl-3-phenylcyclopent-1-enecarboxylate (17a) with trimethylsilyl isothiocyanate gave 7-(3,5-dimethylphenyl)-6,7-dihydro-5H-cyclopenta[e][1,3]oxazine-2,4-dione (12) and 1-benzyl-5-methyl-7-phenyl-2-thioxo-1,2,3,5,6,7-hexahydrocyclopentapyrimidin-4-o ne (18a), respectively. Acid catalyzed ring-closure of 6-(4-methyl-1-phenylpent-3-enyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (26) and radical mediated ring-closure of 1,3-bis(benzyloxymethyl)-5-bromo-6-(1-phenylbut-3-enyl)-1H-pyrimidine-2,4-dione (32a) gave 5,5-dimethyl-8-phenyl-5,6,7,8-tetrahydro-1H-quinazoline-2,4-dione (28) and 1,3-bis(benzyloxymethyl)-5-methyl-7-phenyl-1,5,6,7-tetrahydrocyclopentapyrimidin e-2,4-dione (33), respectively. Annelated emivirine analogues 7-(3,5-dimethylphenyl)-1-ethoxymethyl-1,5,6,7-tetrahydrocyclopentapyrimidine-2,4 -dione (4), 1-ethoxymethyl-5,5-dimethyl-8-phenyl-5,6,7,8-tetrahydro-1H-quinazoline-2,4-dione (5) and 1-ethoxymethyl-5-methyl-7-phenyl-1,5,6,7-tetrahydrocyclopnetapyrimidine-2,4-dion e (6) were obtained in few steps from 12, 28 and 18a/33, respectively. These new analogues can be considered as conformationally locked analogues of emivirine. However, the compounds 4-6 showed lower activities against HIV-1 than emivirine and it is concluded that the locked conformation disfavours activity against HIV-1.
