5,6,7,8-Tetrahydronaphthalen-1-amine as Precursor for Thiazolidi­nones and Benzothiazepinones: Synthesis and Atropisomeric Relationship

Bruna B. Drawanz; Georgia C. Zimmer; Leticia V. Rodrigues; Andressa B. Nörnberg; Manfredo Hörner; Clarissa P. Frizzo; Wilson Cunico

doi:10.1055/s-0036-1590866

Synthesis, Table of Contents

Synthesis 2017; 49(23): 5167-5175
DOI: 10.1055/s-0036-1590866

paper

5,6,7,8-Tetrahydronaphthalen-1-amine as Precursor for Thiazolidinones and Benzothiazepinones: Synthesis and Atropisomeric Relationship

Bruna B. Drawanz

^aLaQuiABio, Centro de Ciências Químicas, Farmacêuticas e de Alimentos, Universidade Federal de Pelotas, Campus Universitário s/no, 96010-900, Pelotas, RS, Brazil Email: wjcunico@yahoo.com.br

,

Georgia C. Zimmer

^bNUQUIMHE, Departamento de Química, Universidade Federal de Santa Maria, Av. Roraima nº 1000, Cidade Universitária, 97105-900,Santa Maria, RS, Brazil

,

Leticia V. Rodrigues

^bNUQUIMHE, Departamento de Química, Universidade Federal de Santa Maria, Av. Roraima nº 1000, Cidade Universitária, 97105-900,Santa Maria, RS, Brazil

,

Andressa B. Nörnberg

^aLaQuiABio, Centro de Ciências Químicas, Farmacêuticas e de Alimentos, Universidade Federal de Pelotas, Campus Universitário s/no, 96010-900, Pelotas, RS, Brazil Email: wjcunico@yahoo.com.br

,

Manfredo Hörner

^cNITRICO, Departamento de Química, Universidade Federal de Santa Maria, Av. Roraima nº 1000, Cidade Universitária, 97105-900,Santa Maria, RS, Brazil

,

Clarissa P. Frizzo

^bNUQUIMHE, Departamento de Química, Universidade Federal de Santa Maria, Av. Roraima nº 1000, Cidade Universitária, 97105-900,Santa Maria, RS, Brazil

,

Wilson Cunico*

^aLaQuiABio, Centro de Ciências Químicas, Farmacêuticas e de Alimentos, Universidade Federal de Pelotas, Campus Universitário s/no, 96010-900, Pelotas, RS, Brazil Email: wjcunico@yahoo.com.br

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Abstract

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Abstract

The one-pot reaction of 5,6,7,8-tetrahydronaphthalen-1-amine, mercaptoacetic acid, and arenealdehydes having strong and weak electron-withdrawing groups gave the corresponding 1,3-thiazolidin-4-ones (47–70%). When arenealdehydes bearing strong and weak electron-donating groups were used as precursors, the 1,4-benzothiazepin-2-ones were obtained (30–72%) by p-TsOH catalysis. All compounds are unknown and were characterized by GC-MS and NMR techniques, and available crystals by X-ray diffraction studies. The atropisomerism phenomenon was observed in several 1,3-thiazolidin-4-ones as confirmed by VTNMR method. The Tc was established as 332 K and the energy required for the interconversion of one atropisomer into another is around 16.8 kcal·mol^–1. Chemical quantum calculation and NOESY displayed that more stable isomer has the tetrahydronaphthalene portion below the five-ring plane. Only a small difference between isomers (–0.21 to –0.84 kcal·mol^–1) was observed by calculated energy.

Key words

thiazolidinone - atropisomer - benzothiazepinone - chemical quantum calculation - X-ray

Full Text

References

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Supplementary Material

Supporting Information

5,6,7,8-Tetrahydronaphthalen-1-amine as Precursor for Thiazolidi­nones and Benzothiazepinones: Synthesis and Atropisomeric Relationship

5,6,7,8-Tetrahydronaphthalen-1-amine as Precursor for Thiazolidinones and Benzothiazepinones: Synthesis and Atropisomeric Relationship