Show/Hide Menu
Hide/Show Apps
Logout
Türkçe
Türkçe
Search
Search
Login
Login
OpenMETU
OpenMETU
About
About
Open Science Policy
Open Science Policy
Open Access Guideline
Open Access Guideline
Postgraduate Thesis Guideline
Postgraduate Thesis Guideline
Communities & Collections
Communities & Collections
Help
Help
Frequently Asked Questions
Frequently Asked Questions
Guides
Guides
Thesis submission
Thesis submission
MS without thesis term project submission
MS without thesis term project submission
Publication submission with DOI
Publication submission with DOI
Publication submission
Publication submission
Supporting Information
Supporting Information
General Information
General Information
Copyright, Embargo and License
Copyright, Embargo and License
Contact us
Contact us
Cyclotrimerization of 'Oxabenzonorbornadiene': Synthesis of syn- and anti-5,6,11,12,17,18-hexahydro-5,18:6,11 : 12,17-triepoxytrinaphthylene
Date
2004-01-01
Author
De Lucchi, O
Dastan, A
Altundas, A
Fabris, F
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
45
views
0
downloads
Cite This
An efficient synthetic route to the concave-shaped, potentially ionophoric syn- and anti-isomers of 5,6,11,12,17,18-hexahydro-5,18:6,11:12,17-triepoxytrinaphthylene (4) was elaborated. Starting from 'oxabenzonorbornadiene' (5), the stannylated precursor 9 was prepared in three steps, followed by cyclotrimerization ;catalyzed by copper(I) thiophene-2-carboxylate (CuTC), which afforded 4 in a synlanti ratio of 5:4.
Subject Keywords
Physical and Theoretical Chemistry
,
Inorganic Chemistry
,
Organic Chemistry
,
Biochemistry
,
Drug Discovery
,
Catalysis
URI
https://hdl.handle.net/11511/56559
Journal
HELVETICA CHIMICA ACTA
DOI
https://doi.org/10.1002/hlca.200490213
Collections
Graduate School of Natural and Applied Sciences, Article
Suggestions
OpenMETU
Core
Synthesis, characterization, crystal and molecular structure of 1,5-Dihydro-2H-cyclopenta[1,2-b : 5,4-b ']dipyridin-2-imine
Baysal, Akin; Durap, Feyyaz; Gumgum, Bahattin; Yildirim, Leyla T.; Ulku, Dincer; Boga, Ayse Dilek; Özkar, Saim (Wiley, 2007-01-01)
The reaction of 1,5-diliydro-2H-cyclopenta[1,2-b:5,4-b'ldipyridin-2-one (3) with an alkylamine (butvlamine, hexylamine or ethylenediamine) yields, quite unexpectedly and in the absence of catalyst, the novel compound 1,5-dihydro-2H-cyclopentafl,2-b:5.4-b']dipyridin-2-imine (4) as the sole, analytically pure, solid product, which was fully characterized. The structure of 4 was unequivocally solved by single-crystal X-ray-diffraction analysis. The compound crystallizes in a monoclinic cell (space group P 2(1/...
Enantioselective synthesis of 2-(2-arylcyclopropyl)glycines: Conformationally restricted homophenylalanine analogs
Demir, Ayhan Sıtkı; Sesenoglu, O; Ulku, D; Arici, C (Wiley, 2004-01-01)
Starting from simple aromatic aldehydes and acetylfuran, (E)-1-(furan-2-yl)-3-arylprop-2-en-1-ones (2) were synthesized in high yields. Cyclopropanation of the C=C bond with trimethylsulfoxonium iodide (Me3SO+I-) furnished (furan-2-yl)(2-arylcyclopropyl)methanones 3 in 90-97% yields. Selective conversion of cyclopropyl ketones to their (E)- and (Z)-oxime ethers 5 and oxazaborolidine-catalyzed stercoselective reduction of the C-N bond followed by separation of the formed diastereoisomers, furnished (2-arylcy...
Chemistry of the benzotropone endoperoxides and their conversion into tropolone derivatives: Unusual endoperoxide rearrangements
Guney, M; Dastan, A; Balcı, Metin (Wiley, 2005-01-01)
The chemistry of two bicyclic endoperoxides, obtained by photooxygenation of 2,3-benzotropone (= 5H-benzocyclohepten-5-one 5) and of its ethyl carboxylate derivative 15, was investigated with the aim of synthesizing the respective benzotropolone derivatives. The reaction of the endoperoxide 10 derived from 5 with thiourea gave the desired benzotropolone, i.e., 6-hvdroxy-5H-benzocyclohepten-5-one (11), in high yield (Scheme 1). On the other hand, the endoperoxide 16 derived from the ethyl carboxylate derivat...
Asymmetric synthesis of novel 1,4-aminoalcohol ligands with norbornene and norbornane backbone: use in the asymmetric diethylzinc addition to benzaldehyde
Tanyeli, Cihangir; ERDEM, Mine; ÇAKIR, Esen; KESKİN, Eda (Elsevier BV, 2007-09-27)
The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene and norbornane backbone was performed starting with (2S, 3R)-(-)-cis-hemiester 1 (98% ee). Chemoselective amination with HMPTA followed by Grignard reactions and subsequent LAH reductions afforded compounds 5a-d. cis-Hemiester 1 was also transformed into chiral ligands 7a-f and 9a-d with the DCC coupling method followed by LAH reduction using acyclic, heterocyclic amines and various aniline derivatives and p-toluenesulfonamide, respectively. ...
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...
Citation Formats
IEEE
ACM
APA
CHICAGO
MLA
BibTeX
O. De Lucchi, A. Dastan, A. Altundas, F. Fabris, and M. Balcı, “Cyclotrimerization of ‘Oxabenzonorbornadiene’: Synthesis of syn- and anti-5,6,11,12,17,18-hexahydro-5,18:6,11 : 12,17-triepoxytrinaphthylene,”
HELVETICA CHIMICA ACTA
, pp. 2364–2367, 2004, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56559.