General and simple method for the synthesis of 3-nitroformazan using arenediazonium tosylates

Pavel V. Petunin; Rashid R. Valiev; Rodion G. Kalinin; Marina E. Trusova; Viktor V. Zhdankin; Pavel S. Postnikov

doi:10.2174/1570179413666160205002843

General and simple method for the synthesis of 3-nitroformazan using arenediazonium tosylates

Pavel V. Petunin, Rashid R. Valiev, Rodion G. Kalinin, Marina E. Trusova, Viktor V. Zhdankin, Pavel S. Postnikov

Chemistry & Biochemistry

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4 Scopus citations

Abstract

A general and simple procedure for the synthesis of 3-nitroformazan using arenediazonium tosylates was developed. This convenient procedure can be applied for the preparation of 3-nitroformazans containing electron-donating or electron-withdrawing groups. First the anomaly 1,5-bis(4-methoxyphenyl)-3-nitroformazan was synthesized as the mixture of TSSC (trans-syn, s-cis) and previously unknown for 3-nitroformazans TASC (transanti, s-cis) isomers. The structure and spectral characteristics of TASC isomer were explained using quantumchemical calculation with TDDFT/B3LYP/6-31++G(d,p) level of theory.

Original language	English (US)
Pages (from-to)	623-628
Number of pages	6
Journal	Current Organic Synthesis
Volume	13
Issue number	4
DOIs	https://doi.org/10.2174/1570179413666160205002843
State	Published - Aug 1 2016

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© 2016 Bentham Science Publishers.

Keywords

Arenediazonium tosylates
Azo-coupling
Diazonium salts
Formazans
Quantum-chemical calculations
TDDFT

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10.2174/1570179413666160205002843

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title = "General and simple method for the synthesis of 3-nitroformazan using arenediazonium tosylates",

abstract = "A general and simple procedure for the synthesis of 3-nitroformazan using arenediazonium tosylates was developed. This convenient procedure can be applied for the preparation of 3-nitroformazans containing electron-donating or electron-withdrawing groups. First the anomaly 1,5-bis(4-methoxyphenyl)-3-nitroformazan was synthesized as the mixture of TSSC (trans-syn, s-cis) and previously unknown for 3-nitroformazans TASC (transanti, s-cis) isomers. The structure and spectral characteristics of TASC isomer were explained using quantumchemical calculation with TDDFT/B3LYP/6-31++G(d,p) level of theory.",

keywords = "Arenediazonium tosylates, Azo-coupling, Diazonium salts, Formazans, Quantum-chemical calculations, TDDFT",

author = "Petunin, {Pavel V.} and Valiev, {Rashid R.} and Kalinin, {Rodion G.} and Trusova, {Marina E.} and Zhdankin, {Viktor V.} and Postnikov, {Pavel S.}",

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T1 - General and simple method for the synthesis of 3-nitroformazan using arenediazonium tosylates

AU - Petunin, Pavel V.

AU - Valiev, Rashid R.

AU - Kalinin, Rodion G.

AU - Trusova, Marina E.

AU - Zhdankin, Viktor V.

AU - Postnikov, Pavel S.

PY - 2016/8/1

Y1 - 2016/8/1

N2 - A general and simple procedure for the synthesis of 3-nitroformazan using arenediazonium tosylates was developed. This convenient procedure can be applied for the preparation of 3-nitroformazans containing electron-donating or electron-withdrawing groups. First the anomaly 1,5-bis(4-methoxyphenyl)-3-nitroformazan was synthesized as the mixture of TSSC (trans-syn, s-cis) and previously unknown for 3-nitroformazans TASC (transanti, s-cis) isomers. The structure and spectral characteristics of TASC isomer were explained using quantumchemical calculation with TDDFT/B3LYP/6-31++G(d,p) level of theory.

AB - A general and simple procedure for the synthesis of 3-nitroformazan using arenediazonium tosylates was developed. This convenient procedure can be applied for the preparation of 3-nitroformazans containing electron-donating or electron-withdrawing groups. First the anomaly 1,5-bis(4-methoxyphenyl)-3-nitroformazan was synthesized as the mixture of TSSC (trans-syn, s-cis) and previously unknown for 3-nitroformazans TASC (transanti, s-cis) isomers. The structure and spectral characteristics of TASC isomer were explained using quantumchemical calculation with TDDFT/B3LYP/6-31++G(d,p) level of theory.

KW - Arenediazonium tosylates

KW - Azo-coupling

KW - Diazonium salts

KW - Formazans

KW - Quantum-chemical calculations

KW - TDDFT

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JO - Current Organic Synthesis

JF - Current Organic Synthesis

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ER -

General and simple method for the synthesis of 3-nitroformazan using arenediazonium tosylates

Abstract

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