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Regioselectivity of the substitution for the nitro group in 2,4,6-trinitrobenzonitrile under the action of thiols. The synthesis of 4,6-dinitro derivatives of benzoannelated sulfur-containing heterocycles

Igor L'vovich Dalinger 1
Igor L'vovich Dalinger
, 
Tat'yana Ivanovna Cherkasova 1
Tat'yana Ivanovna Cherkasova
, 
Valerian Matveevich Khutoretskii 1
Valerian Matveevich Khutoretskii
, 
Svyatoslav Arkad'evich Shevelev 1
Svyatoslav Arkad'evich Shevelev
10.1070/MC2000v010n02ABEH001220
Published 2000-03-30
Communication , Volume 10, Issue 2, 72-73
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Dalinger I. L. et al. Regioselectivity of the substitution for the nitro group in 2,4,6-trinitrobenzonitrile under the action of thiols. The synthesis of 4,6-dinitro derivatives of benzoannelated sulfur-containing heterocycles // Mendeleev Communications. 2000. Vol. 10. No. 2. pp. 72-73.
GOST all authors (up to 50) Copy
Dalinger I. L., Cherkasova T. I., Khutoretskii V. M., Shevelev S. A. Regioselectivity of the substitution for the nitro group in 2,4,6-trinitrobenzonitrile under the action of thiols. The synthesis of 4,6-dinitro derivatives of benzoannelated sulfur-containing heterocycles // Mendeleev Communications. 2000. Vol. 10. No. 2. pp. 72-73.
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TY - JOUR
DO - 10.1070/MC2000v010n02ABEH001220
UR - https://mendcomm.colab.ws/publications/10.1070/MC2000v010n02ABEH001220
TI - Regioselectivity of the substitution for the nitro group in 2,4,6-trinitrobenzonitrile under the action of thiols. The synthesis of 4,6-dinitro derivatives of benzoannelated sulfur-containing heterocycles
T2 - Mendeleev Communications
AU - Dalinger, Igor L'vovich
AU - Cherkasova, Tat'yana Ivanovna
AU - Khutoretskii, Valerian Matveevich
AU - Shevelev, Svyatoslav Arkad'evich
PY - 2000
DA - 2000/03/30
PB - Mendeleev Communications
SP - 72-73
IS - 2
VL - 10
ER -
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@article{2000_Dalinger,
author = {Igor L'vovich Dalinger and Tat'yana Ivanovna Cherkasova and Valerian Matveevich Khutoretskii and Svyatoslav Arkad'evich Shevelev},
title = {Regioselectivity of the substitution for the nitro group in 2,4,6-trinitrobenzonitrile under the action of thiols. The synthesis of 4,6-dinitro derivatives of benzoannelated sulfur-containing heterocycles},
journal = {Mendeleev Communications},
year = {2000},
volume = {10},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2000v010n02ABEH001220},
number = {2},
pages = {72--73},
doi = {10.1070/MC2000v010n02ABEH001220}
}
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Dalinger, Igor L'vovich, et al. “Regioselectivity of the substitution for the nitro group in 2,4,6-trinitrobenzonitrile under the action of thiols. The synthesis of 4,6-dinitro derivatives of benzoannelated sulfur-containing heterocycles.” Mendeleev Communications, vol. 10, no. 2, Mar. 2000, pp. 72-73. https://mendcomm.colab.ws/publications/10.1070/MC2000v010n02ABEH001220.

Abstract

Conditions for the regioselective substitution for a nitro group in the ortho-position in 2,4,6-trinitrobenzonitrile under the action of thiols (PhCH2SH, HSCH2CO2Et or PhSH) in the presence of K2CO3 or KOH were found, and the intramolecular cyclization of the ortho-fragments –SX and –CN (X = Cl or CH2CO2Et) was performed to afford 3-chloro-4,6-dinitrobenzo[d]isothiazole and 3-amino- 2-ethoxycarbonyl-4,6-dinitrobenzo[b]thiophene, respectively.

References

1.
10.1070/MC2000v010n02ABEH001220_bib1
Tartakovsky
Conversion Concepts for Commercial Applications and Disposal Technologies of Energetic Systems, 1997