Regioselective synthesis of the 3,4-dihydrofuro[3,2-d]pyrimidin-2(1H)-one skeleton: a new class of compound

2009-08-01
Koza, Gani
Ozcan, Sevil
ŞAHİN, Ertan
Balcı, Metin
We hereby report the first preparation of the 3,4-dihydrofuro[3,2-d]pyrimidin-2(1H)-one skeleton formed by two controlled Curtius rearrangements of the corresponding acyl azides, prepared from 2-(2-methoxy-2-oxoethyl)furan-3-carboxylate via the hydrazide. Rearrangement of the acyl azides followed by trapping by nucleophiles and intramolecular trapping provided the target compounds.

Suggestions

Regioselective Synthesis of the 5,6-Dihydro-4H-furo[2,3-c]pyrrol-4-one Skeleton: A New Class of Compounds
Koza, Gani; Karahan, Emrah; Balcı, Metin (Wiley, 2010-01-01)
We hereby report the first preparation of the 5,6-dihydro-4H-furo[2.3-c]pyrrol-4-one (3) and its derivatives starting from methyl 3-(methoxycarbonyl)furnan-2-acetate (8). The ester functionality connected to the methylene group was regiospecifically converted to the desired monohydrazide 9. Conversion of 9 into the acyl azide In followed by Curtius rearrangement gave the corresponding isocyanate derivative 11 (Scheme 2). Reaction of 11 with different nucleophiles produced urethane and urea derivatives (Sche...
Regioselective alkylation of dianions of cyclic 1.3-diketones via their monodimethylhydrazones. Synthesis of C-4 substituted cyclic 1.3-diketones
Enders, Dieter; Demir, Ayhan Sıtkı (Elsevier BV, 1989-1)
Cyclic 1.3-diketones are transformed into the corresponding monodimethylhydrazones, which can be alkylated regioselectively at C-4 via dianions with various alkyl halides. The regioselective alkylation of cyclic 1.3-diketones 1, to 4-substituted derivatives 4 is described.
Indium triflate-catalyzed coupling of indoles with acyl phosphonates: synthesis of bis(indolyl)methane phosphonates
Dasbasi, Teslima; Polat-Cakir, Sidika; Abdullah, Meysun; Demir, Ayhan Sıtkı (Elsevier BV, 2011-05-13)
The coupling reaction of N-methylindole with alkyl and aryl phosphonate is described. The reaction works in the presence of 10 mol % of indium triflate and furnished bis(indolyl)methane phosphonates in good yield and high selectivity.
Manganese(III) acetate-mediated oxidative coupling of phenylhydrazines with furan and thiophene: a novel method for hetero biaryl coupling
Demir, Ayhan Sıtkı; Reis, O; Emrullahoglu, M (Elsevier BV, 2002-09-30)
A convenient new method for the arylation of furan and thiophene with arylhydrazine and manganese(III) acetate is described. Oxidation of arylhydrazines with Mn(III) acetate in furan or thiophene affords the corresponding 2-aryl-substituted furans and thiophenes in good yield using commercially available materials; access to 2-substituted heterobiaryls works selectively, and coupling occurs with loss of the hydrazine moiety.
Regioselectivity in the ene-reaction of singlet oxygen with cyclic alkenes: photooxygenation of methyl-substituted 1,4-cyclohexadiene derivatives
Yardimci, Sengul Dilem; Kaya, Nihal; Balcı, Metin (Elsevier BV, 2006-11-13)
The photooxygenation of the 1-methyl-, 2,3-dimethyl-, and 1,4-dimethylcyclohexa-1,4-dienes, which are readily available through Birch reduction, yielded the corresponding ene-products. The formed endocyclic dienes were trapped by the addition of singlet oxygen to give the corresponding bicyclic endoperoxy hydroperoxides. In the case of 1-methylcyclohexa-1,4-diene and 1,4-dimethylcyclohexa-1,4,-diene, the cis-effect determined the product distribution. Photooxygenation of 2,3-dimethylcyclohexa-1,4-dienes gav...
Citation Formats
G. Koza, S. Ozcan, E. ŞAHİN, and M. Balcı, “Regioselective synthesis of the 3,4-dihydrofuro[3,2-d]pyrimidin-2(1H)-one skeleton: a new class of compound,” TETRAHEDRON, pp. 5973–5976, 2009, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51306.