Hetero Diels-Alder reactions of acyl phosphonates: synthesis of glycosyl type phosphonates

Date

2011-04-01

Author

Polat-Cakir, Sidika
Demir, Ayhan Sıtkı

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

234
views

0
downloads

We have prepared glycosyl type phosphonates via hetero Diels-Alder (HDA) reactions of acyl phosphonates with electron rich dienes. HDA reactions of acyl phosphonates with Danishefsky's diene required thermal activation to yield the desired dihydropyranones in good yield (70-91%). The reactions with Brassard's diene involved Lewis acid promotion to yield the corresponding lactones, though in moderate yield (33-69%).

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/62610

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2011.02.007

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

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.
Intermolecular heterocyclization of alkynones with 2-mercaptoacetaldehyde under metal-free conditions: synthesis of 2,3-disubstituted thiophenes Vatansever, Erol Can; Kilic, Kubra; Ozer, Merve Sinem; KOZA, GANİ; Menges, Nurettin; Balcı, Metin (Elsevier BV, 2015-09-30) A concise and regioselective approach for the synthesis of 2,3-disubstituted thiophene derivatives has been developed. The synthetic strategy relies on the reaction of an in situ generated 2-mercaptoacetaldehyde with various alkynones. Furthermore, we calculated the energy gap between the HOMO and the LUMO orbitals of all compounds and observed that the introduction of a strong electron-withdrawing group decreased the HOMO-LUMO energy gap.
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.
Divergent synthesis of polysubstituted isoxazoles, isoxazoline N-oxides, and dihydroisoxazoles by a one-pot cascade reaction Rouf, Abdul; ŞAHİN, Ertan; Tanyeli, Cihangir (Elsevier BV, 2017-01-26) An efficient one-pot synthesis of a new class of 3,4,5-trisubstituted isoxazoline N-oxides/isoxazoles and dihydroisoxazoles is developed by a green approach from aromatic and aliphatic aldehydes by controlling the reaction conditions. Aldehydes were reacted with ethyl nitroacetate in the presence of DABCO as a catalyst under ultrasonication. In aromatic aldehydes, isoxazoline N-oxides were obtained exclusively when the reaction was carried out at 40 degrees C, but raising the temperature to 80 degrees C iso...
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.

Citation Formats

S. Polat-Cakir and A. S. Demir, “Hetero Diels-Alder reactions of acyl phosphonates: synthesis of glycosyl type phosphonates,” TETRAHEDRON, pp. 2396–2401, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/62610.