The chemistry of homophthalic acid: a new synthetic strategy for construction of substituted isocoumarin and indole skeletons

Date

2008-06-02

Author

Oezcan, Sevil
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

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 reactions of these products gave first an indolinone derivative, which underwent further intermolecular condensation to give substituted indole derivatives. However, when the condensation reaction was carried out in the presence of acetic anhydride, the intermolecular reactions were suppressed. This methodology opens up a new way of synthesizing of various five-membered ring substituted indole derivatives.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/57560

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2008.03.097

Collections

Graduate School of Natural and Applied Sciences, Article

Suggestions

OpenMETU
Core

The synthesis of unusual isocoumarin derivatives: the chemistry of homophthalic acid Ozcan, Sevil; Sahin, Ertan; Balcı, Metin (Elsevier BV, 2007-03-19) 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.
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...
Unusual oxidative free-radical additions of 1,3-dicarbonyl compounds to benzonorbornadiene and oxabenzonorbornadiene Cahskan, R; Pekel, T; Watson, WH; Balcı, Metin (Elsevier BV, 2005-09-12) Benzonorbornadiene and oxabenzonorbornadiene were reacted with dimedone and acetylacetone in the presence of Mn(OAc)(3) and Cu(OAc)(2). The reaction of benzonorbornadiene with dimedone gave the dihydrofuran addition product, whereas the reaction with acetylacetone produced, in addition to the dihydrofuran derivative, a rearranged product. On the other hand, oxanorbornadiene gave unusual products such as the cyclopropanated compound and the product arising from the addition of two moles of dimedone. The mech...
Manganese(III)-mediated oxidative free-radical additions of 1,3-dicarbonyl compounds to homobenzonorbornadiene and benzobarrelene: mechanistic studies Ali, Mohamed Fadelalla; Caliskan, Rasit Ali; ŞAHİN, Ertan; Balcı, Metin (Elsevier BV, 2009-02-14) Homobenzonorbornadiene and benzobarrelene were reacted with dimedone/acetylacetone and Mn(OAc)(3) in the presence of Cu(OAc)(2) in acetic acid. Mainly rearranged products having a [2.2.2]skeleton and the nonrearranged dihydrofuran derivatives were obtained. These observations clearly indicated that the second oxidation takes place before the cyclization reaction. Furthermore, intramolecular tandem oxidations were observed where unusually oxyl radicals attack the double bond to form the products. The mechani...
An in depth study of the formation of new tetrathiafulvalene derivatives from 1,8-diketones Turksoy, F; Wallis, JD; Tunca, U; Ozturk, T (Elsevier BV, 2003-10-06) A detailed study of the reactions of phosphorus pentasulfide and Lawesson's reagent with a series of 4,5-bis(RCOCHS)-1,3-dithiole-2-thiones (R-Ph, 4-MeOC6H4, 4-Br C6H4, Me) has been carried out. These reactions lead to fusion of either an unsaturated 1,4-dithiin ring or a thiophene to the dithiole; the former in higher yield, while the latter is a significant product in the reactions with Lawesson's reagent; as well as small amounts of minor products. A mechanistic rationalization of these products is discu...

Citation Formats

S. Oezcan and M. Balcı, “The chemistry of homophthalic acid: a new synthetic strategy for construction of substituted isocoumarin and indole skeletons,” TETRAHEDRON, pp. 5531–5540, 2008, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57560.