Synthesis of N-tosyl-5-methyl-3-methylidene-2-ethylindole

Skladchikov, D. A.; Гатауллин, Р. Р.

doi:10.1134/s107036321302028x

Cited by 3 publications

(1 citation statement)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…19 Authors who have identified atropisomerism in their compounds cite the NMR duplication signals as the most common proof of occurrence. 20,21 In benzothiazepinones 7f, 7j-m, this phenomenon was not observed.…”

Section: Syn Thesis Scheme 3 Synthesis Of 14-benzothiazepin-2-ones 7mentioning

confidence: 98%

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

et al. 2017

View full text Add to dashboard Cite

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.

show abstract

Section: Syn Thesis Scheme 3 Synthesis Of 14-benzothiazepin-2-ones 7mentioning

confidence: 98%

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

et al. 2017

View full text Add to dashboard Cite

show abstract

Synthesis of N-sulfonated N-benzoazoles and their use in medicinal chemistry

Elgemeie

Azzam

Zaghary

et al. 2022

N-Sulfonated-N-Heterocycles

View full text Add to dashboard Cite

Synthesis of N-Tosylates of 4-Methoxy-1,2,3,4-tetrahydrocarbazole and 2-(6-Methoxy-1-cycloalken-1-yl)anilines

et al. 2018

View full text Add to dashboard Cite

Synthesis of N-tosyl-5-methyl-3-methylidene-2-ethylindole

Cited by 3 publications

References 9 publications

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

Synthesis of N-sulfonated N-benzoazoles and their use in medicinal chemistry

Synthesis of N-Tosylates of 4-Methoxy-1,2,3,4-tetrahydrocarbazole and 2-(6-Methoxy-1-cycloalken-1-yl)anilines

Contact Info

Product

Resources

About

Synthesis of N-tosyl-5-methyl-3-methylidene-2-ethylindole

Cited by 3 publications

References 9 publications

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

Synthesis of N-sulfonated N-benzoazoles and their use in medicinal chemistry

Synthesis of N-Tosylates of 4-Methoxy-1,2,3,4-tetrahydrocarbazole and 2-(6-Methoxy-1-cycloalken-1-yl)anilines

Contact Info

Product

Resources

About

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