The synthesis of unusual isocoumarin derivatives: the chemistry of homophthalic acid

2007-03-19
Ozcan, Sevil
Sahin, Ertan
Balcı, Metin
Show full item record
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
194
views
0
downloads
Homophthalic acid was reacted with thionyl chloride/DMF and ethyl chloroformate/NEt3 in the presence and absence of NaN3. In all cases completely different isocoumarin derivatives were obtained. These unusual isocournarin derivatives were characterized and their mechanism of formation is discussed.
Organic Chemistry, Biochemistry, Drug Discovery
https://hdl.handle.net/11511/51286
TETRAHEDRON LETTERS
Graduate School of Natural and Applied Sciences, Article

Suggestions

The chemistry of homophthalic acid: a new synthetic strategy for construction of substituted isocoumarin and indole skeletons
Oezcan, Sevil; Balcı, Metin (Elsevier BV, 2008-06-02)
Homophthalic acid was reacted with thionylchloride/DMF and chloroethylformate/NEt(3) in the presence and absence of NaN(3). in all cases completely different isocoumarin derivatives were obtained. These unusual isocoumarin derivatives were isolated and characterized and their formation mechanisms are discussed. The homophthalic acid monomethyl ester was converted into the corresponding isocyanate. Reaction of the isocyanate with different amines produced the urea derivatives. Base-supported condensation rea...
Unusual manganese(III)-mediated oxidative free-radical additions of Meldrum's acid and dimethyl malonate to benzonorbornadiene and oxabenzonorbornadiene
ÇALIŞKAN, Raşit; Nohut, Neslihan; Yilimaz, Ozlem; ŞAHİN, Ertan; Balcı, Metin (Elsevier BV, 2017-01-26)
Benzonorbornadiene and 7-oxabenzonorbornadiene were reacted with Meldrum's acid and dimethyl malonate in the presence of Mn(OAc)(3) and Cu(OAc)(2) in acetic acid. The reaction of benzonorbornadiene with Meldrum's acid gave a naphthalene derivative whereas the reaction with dimethyl malonate formed rearranged products derived from a carbocation intermediate. However, the reaction of 7-oxabenzonorbornadiene with Meldrum's acid gave two nonrearranged products. On the other hand, the reaction with dimethyl malo...
A novel synthesis of 1,2,4-oxadiazoles and isoxazoles
KIVRAK, Arif; Zora, Metin (Elsevier BV, 2014-01-28)
A novel synthesis of 1,2,4-oxadiazoles and isoxazoles is described by utilizing the reactions between amidoximes and alpha,beta-alkynic aldehydes and/or ketones. Conjugate addition products, obtained from amidoximes and alpha,beta-alkynic aldehydes and/or ketones, afford 1,2,4-oxadiazoles and isoxazoles when treated with bases and acids, respectively. 1,2,4-Oxadiazoles can also be synthesized directly from amidoximes and alpha,beta-alkynic aldehydes in a one-pot manner under basic conditions. The reactions ...
Reactions of acyl phosphonates with organoaluminum reagents: a new method for the synthesis of secondary and tertiary alpha-hydroxy phosphonates
Seven, Ozlem; Polat-Cakir, Sidika; Hossain, Md. Shakhawoat; Emrullahoglu, Mustafa; Demir, Ayhan Sıtkı (Elsevier BV, 2011-05-13)
The reactions of organoaluminum reagents (trimethylaluminum, triethylaluminum, etc.) with aryl and alkyl acyl phosphonates, which lead to the formation of alpha-hydroxy phosphonates in moderate to good yields, are reported. This method provides easy access to secondary and tertiary alpha-hydroxy phosphonates depending on the reaction conditions. The reactions of triethylaluminum with a series of acyl phosphonates at 0 degrees C gave the secondary alpha-hydroxy phosphonates, while at -100 degrees C they affo...
Highly efficient and selective olefination of acyl phosphonates with ethyl diazoacetate catalyzed by a cobalt(II) porphyrin complex
Erturk, Erkan; Demir, Ayhan Sıtkı (Elsevier BV, 2008-08-04)
The cobalt(II) porphyrin complex (CoTPP) was found to be an efficient catalyst for the Wittig type olefination of acyl phosphonates with ethyl diazoacetate (EDA) in the presence of triphenylphosphine (Ph(3)P). By using this one pot methodology under mild conditions, densely functionalized vinyl phosphonates were obtained in high yields and high E/Z selectivities in relatively short reaction times. A rather broad substrate spectrum and steric influence on the reaction rate were observed.
Citation Formats
S. Ozcan, E. Sahin, and M. Balcı, “The synthesis of unusual isocoumarin derivatives: the chemistry of homophthalic acid,” TETRAHEDRON LETTERS, pp. 2151–2154, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51286.
METU IIS - Integrated Information Service open@metu.edu.tr