Application of the systems chemistry approach on the ammonolysis of 1-ethoxycarbonyl- and 1-phenoxycarbonyl-3-(2-thienyl)oxindoles. A method to predict reactivity

Zoltán Mucsi, Márta Porcs-Makkay, Gyula Simig, I. Csizmadia, Balázs Volk

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The routine prediction of the reactivity of a complex, multifunctional molecule is a challenging and time-consuming procedure. In the last step of the synthesis of the well-known drug substance tenidap, a nonexpected difference was observed between the reactivities of two closely related carbamate moieties, the N-ethoxycarbonyl and the N-phenoxycarbonyl group. A detailed kinetic study, necessitating a significant computational effort, is described in the present paper for this reaction step. On the other hand, the systems chemistry concept, by analyzing the details of the electronic structure and the connections between functional groups in a fast and simple way, is also able to answer this question using various "-icity"? parameters (aromaticity, carbonylicity, olefinicity). The complete systems chemistry approach involves all these conjugativicity parameters, while its further simplified version is based on only one key parameter, which is carbonylicity in the present case. The above methods were compared in terms of their predictive power. The results show that the systems chemistry concept, even its one-parameter version, is applicable for the characterization of this challenging reactivity issue.

Original languageEnglish
Pages (from-to)7282-7290
Number of pages9
JournalJournal of Organic Chemistry
Volume77
Issue number17
DOIs
Publication statusPublished - Sep 7 2012

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Carbamates
Functional groups
Electronic structure
Molecules
Kinetics
Pharmaceutical Preparations
oxindole
tenidap

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Application of the systems chemistry approach on the ammonolysis of 1-ethoxycarbonyl- and 1-phenoxycarbonyl-3-(2-thienyl)oxindoles. A method to predict reactivity. / Mucsi, Zoltán; Porcs-Makkay, Márta; Simig, Gyula; Csizmadia, I.; Volk, Balázs.

In: Journal of Organic Chemistry, Vol. 77, No. 17, 07.09.2012, p. 7282-7290.

Research output: Contribution to journalArticle

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