Chemistry of bicyclic endoperoxides derived from dihydropyridine derivatives: Attempted synthesis of polyhydroxypiperidine derivatives

Date

2006-01-01

Author

Salamci, Emine
Bayram, Beyhan
Balcı, Metin

Metadata

Show full item record

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

Item Usage Stats

163
views

0
downloads

To achieve the synthesis of azasugar derivatives with the utilization of singlet oxygen, pyridine was used as the starting material. The reduction of pyridine followed by a singlet oxygen reaction afforded cyclic aza-endoperoxides (14 and 16). However, many attempts were made to convert the azaendoperoxides to the corresponding di- and triacetates without success. However, the base-catalyzed rearrangement of 14 gave unprecedented rearrangement products 23 and 24.

Subject Keywords

Azasugar derivatives, Amino sugars, Singlet oxygen, Bicyclic endoperoxides

URI

https://hdl.handle.net/11511/55974

Journal

TURKISH JOURNAL OF CHEMISTRY

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

Synthesis of n-(2-propylphenyl) substituted chiral amino alcohols and their usage in enantioselective diethylzinc addition reactions Günler, Zeynep İnci; Tanyeli, Cihangir; Department of Chemistry (2011) IChiral 1,2-amino alcohols were synthesized via newly developed “intramolecular unsaturation transfer” using cyclohexanone, propargyl bromide, and various chiral amino alcohols as starting components. These amino alcohols can be potential chiral ligands for many asymmetric transformation reactions. Therefore, their effectiveness as chiral ligands in diethylzinc addition to benzaldehyde and N-diphenylphosphinoyl imines were tested. Various parameters including temperature, solvent, ligand amount etc. were sc...
Synthesis of chiral acetoxy lactones via the Baeyer-Villiger oxidation of cyclic aromatic acetoxy ketones Demir, Ayhan Sıtkı; Aybey, Asuman (Elsevier BV, 2008-12-01) The alpha-acetoxylation of indanones and tetralones by using Mn(OAc)(3) followed by the enzyme catalyzed kinetic resolution of acetoxy ketones furnished both of the enantiomers of alpha-acetoxy ketones in good chemical and optical yields. The Baeyer-Villiger oxidation of alpha-acetoxy ketones with m-CPBA, CF(3)SO(3)H, and CH(2)O(2), at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords ph...
Synthesis of various camphor-based chiral pyridine derivatives Tanyeli, Cihangir; Isik, M (Elsevier BV, 2004-07-19) (+)-beta-Hydroxymethylenecamphor 1 and enamines 2a-e were transformed into chiral camphor-based pyridine derivatives 3a-e via a tandem condensation reaction in good yields.
Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton BARAN, ARİF; Bekarlar, Merve; Aydin, Gokay; NEBİOĞLU, MEHMET; ŞAHİN, Ertan; Balcı, Metin (2012-02-03) 1,3,3a,7a-Tetrahydro-2-benzofuran was used as key compound for the synthesis of various bishomoinositol derivatives. The diene was subjected to an epoxidation reaction for further functionalization of the diene unit. The bisepoxide obtained was submitted to a ring-opening reaction with acid in the presence of water. Various bishomoinositols were synthesized. However, when the reaction was carried out in the presence of acetic anhydride, a substituted 3-oxabicyclo[3.3.1]nonane skeleton was formed. The mechan...
Oxidation of some alkoxy-cycloheptatriene derivatives: unusual formation of furan and furanoids from cycloheptatrienes Coskun, Ahmet; Guney, Murat; Dastan, Arif; Balcı, Metin (Elsevier BV, 2007-06-04) The oxidation of some alkoxy tropone and tropone ketal derivatives with singlet oxygen and m-chloroperbenzoic acid was investigated. In most cases furan and furanoid derivatives were isolated. The structures of the formed products were determined by means of spectral data and the formation mechanism of these unusual products is discussed.

Citation Formats

E. Salamci, B. Bayram, and M. Balcı, “Chemistry of bicyclic endoperoxides derived from dihydropyridine derivatives: Attempted synthesis of polyhydroxypiperidine derivatives,” TURKISH JOURNAL OF CHEMISTRY, pp. 441–449, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/55974.