Synthesis of Novel 1,4-Benzoquinone-Containing 1,2,3-Triazoles: An Entry Into a New Library

Algi, Fatih
Balcı, Metin
A heretofore unexplored library of 1,4-benzoquinone-containing 1,2,3-triazoles was prepared by the application of a highly regioselective copper(1)-catalyzed process. Furthermore, the utilization of this novel triazole-1,4-benzoquinone system as an interesting class of extended, branched molecules for the construction of new supramolecular architectures is presented.


Asymmetric synthesis of norbornene based 1,4-amino alcohol derivatives and applications in asymmetric transformations
Sünbül, Murat; Tanyeli, Cihangir; Department of Chemistry (2005)
The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene backbone was performed starting with simple and cheap anhydride 30. Quinine-mediated desymmetrization of anhydride 30 with methanol resulted in (2S,3R)-(-)-cis-hemiester 31 (98% e.e.). Chemoselective amination with HMPTA and NH4OH followed by LAH reduction afforded (2S,3R)-(+)-36 and (2S,3R)-(-)-37, respectively. The amidoester (2S,3R)-(-)-32 was transformed into chiral ligand (2S,3R)-(-)-35 with Grignard reaction followed by LAH reduction. T...
Synthesis of 1,4-Thiazepines
Kelgokmen, Yılmaz; Zora, Metin (American Chemical Society (ACS), 2018-08-03)
An efficient, general, and unprecedented methodology for the synthesis of 2-methylene-2,3-dihydro-1,4-thiazepines from N-propargylic beta-enaminones is described. Initially, N-propargylic beta-enaminones were thionated with Lawesson's reagent in good to high yields, and then the resulting N-propargylic beta-enaminothiones were subjected to electrophilic cyclization. When treated with zinc chloride in refluxing chloroform, Npropargylic beta-enaminothiones underwent electrophilic cyclization to yield 2-methyl...
Design and synthesis of functional molecular squares
Akpınar, Handan; Akkaya, Engin Umut; Department of Chemistry (2006)
Self-assembly has big importance in synthesizing supramolecular structures. Highly fluorescent molecular squares with boradiazaindacene (BODIPY) building blocks were obtained via usage of metal driven self-asembly. The boradiazaindacene units were connected with the Pd(II) complex unit enforcing a near-90 degree angle between the building blocks. Thus, we believe we have the first example of BODIPY carrying fluorescent squares. With collective experience in BODIPY chemistry in our group, we may have the fir...
Development of acyl anion precursors and their applications
Reis, Ömer; Demir, Ayhan Sıtkı; Department of Chemistry (2005)
This thesis presents the development of new acyl anion precursors and their applications. The main concern of this thesis was to make use of acyl anion precursors in catalytic bond forming reactions. Toward this aim, previously known cyanide ion catalyzed cleavage of benzils was investigated in scope and efficiency in unsymmetrical benzoin condensation. Although benzils were proved to be useful entities as acyl anion precursors in benzoin condensation, they suffer some major drawbacks. Therefore acylphospho...
A new approach for the synthesis of spiro and gem-dimethyl-substituted 1,4-oxazepines from N-propargylic beta-enaminones
Karadeniz, Eda; Kelgökmen, Yılmaz; Zora, Metin (Wiley, 2020-11-01)
An efficient and general method for the synthesis of spiro-1,4-oxazepines and 3,3-dimethyl-1,4-oxazepines is reported. When treated with ZnI2 and AgSbF6 in refluxing DCE, cyclohexane-embedded N-propargylic beta-enaminones underwent 7-exo-dig cyclization to afford spiro-1,4-oxazepines, specifically 12-methylene-11-oxa-7-azaspiro[5.6]dodeca-7,9-dienes, in good to high yields. Accordingly, N-(1,1-dimethyl)propargylic beta-enaminones produced 3,3-dimethyl-1,4-oxazepines. Cyclization was found to be general for ...
Citation Formats
F. Algi and M. Balcı, “Synthesis of Novel 1,4-Benzoquinone-Containing 1,2,3-Triazoles: An Entry Into a New Library,” SYNTHESIS-STUTTGART, pp. 1341–1347, 2009, Accessed: 00, 2020. [Online]. Available: