Synthesis of a New 2,3-Diaminoconduritol with Conduritol F Structure

Ekmekci, Zeynep
Balcı, Metin
A new 2,3-diaminoconduritol derivative with the conduritol F structure was prepared starting from cyclohexa-1,4-diene. Initially, a lactam, prepared by the cycloaddition of chlorosulfonyl isocyanate (CSI) to cyclohexa-1,4-diene, was converted into an amino acid. The conversion of the acid functionality into an isocyanate resulted in the formation of an imidazolidinone derivative, formed by an intramolecular cyclization. In the second part of this work, the known anhydride, 3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione was successfully converted into the desired bis(carbamate). The bromination of the double bond in the six-membered ring followed by a DBU-induced (DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene) HBr elimination furnished the symmetrical diene. The photooxygenation of the diene unit afforded the bicyclic endoperoxide. The reaction of the endoperoxide with thiourea followed by acetylation resulted in the formation of a syn-configured diacetate. The deprotection of the urethane and acetate groups gave the new 2,3-diaminoconduritol with the conduritol F structure.


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Ten different N-propargyl pyrrole derivatives having various substituents at the C-2 position were synthesized. These derivatives were converted into indolizine derivatives by the [2+2] cycloaddition reaction of pyrrole N-allene, forming in situ, by heating in PrOH in basic medium. The structures were characterized by NMR and X-ray crystallography. The N-propargylated derivatives smoothly underwent intermolecular cyclizations to produce indolizine derivatives in good yields. We proposed a radical mechanism ...
Synthesis of Pyrazoles via Cul-Mediated Electrophilic Cyclizations of alpha,beta-Alkynic Hydrazones
Zora, Metin (2011-11-18)
Synthesis of pyrazoles via electrophilic cyclization of alpha,beta-alkynic hydrazones by copper(I) iodide is described. When treated with copper(I) iodide in the presence of triethylamine in refluxing acetonitrile, alpha,beta-alkynic hydrazones, prepared readily from hydrazines and propargyl aldehydes and ketones, undergo electrophilic cyclization to afford pyrazole derivatives in good to excellent yields. The reaction appears to be general for a variety of alpha,beta-alkynic hydrazones and tolerates the pr...
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A convergent, multistep protocol was employed for the synthesis of a Janus-type multivalent donoracceptor system. The synthetic approach is based on a Sonogashira cross-coupling of two differently ferrocene-(Fc) substituted dendrons and a final sixfold [2 + 2] cycloaddition-retroelectrocyclization (CA-RE) reaction with tetracyanoethene, which occurs regioselectively at only one of the rigidly linked dendrons. The structural and optoelectronic properties of the compounds were investigated by X-ray analysis, ...
Synthesis and structure elucidation of bromination products from dibromohomobenzonorbornadienes: high temperature bromination - Part 17
Kazaz, C; Dastan, A; Balcı, Metin (Wiley, 2005-01-01)
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Citation Formats
Z. Ekmekci and M. Balcı, “Synthesis of a New 2,3-Diaminoconduritol with Conduritol F Structure,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, pp. 4988–4995, 2012, Accessed: 00, 2020. [Online]. Available: