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Unexpected formation of 4-hydroxy-6-nitroindoles in the intramolecular cyclization of O-(3-amino-5-nitrophenyl)ketoximes

Sergei Sergeyevich Vorob'ev 1
Sergei Sergeyevich Vorob'ev
, 
Mikhail Dmitrievich Dutov 1
Mikhail Dmitrievich Dutov
, 
Irina Anatol'evna Vatsadze 1
Irina Anatol'evna Vatsadze
, 
Vadim Vadimovich Kachala 1
Vadim Vadimovich Kachala
, 
Yurii Andreevich Strelenko 1
Yurii Andreevich Strelenko
, 
Andrei A Sedov 1
Andrei A Sedov
, 
Svyatoslav Arkad'evich Shevelev 1
Svyatoslav Arkad'evich Shevelev
10.1016/j.mencom.2007.03.026
Published 2007-03-15
Communication , Volume 17, Issue 2, 128-129
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Vorob'ev S. S. et al. Unexpected formation of 4-hydroxy-6-nitroindoles in the intramolecular cyclization of O-(3-amino-5-nitrophenyl)ketoximes // Mendeleev Communications. 2007. Vol. 17. No. 2. pp. 128-129.
GOST all authors (up to 50) Copy
Vorob'ev S. S., Dutov M. D., Vatsadze I. A., Kachala V. V., Strelenko Y. A., Sedov A. A., Shevelev S. A. Unexpected formation of 4-hydroxy-6-nitroindoles in the intramolecular cyclization of O-(3-amino-5-nitrophenyl)ketoximes // Mendeleev Communications. 2007. Vol. 17. No. 2. pp. 128-129.
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TY - JOUR
DO - 10.1016/j.mencom.2007.03.026
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.03.026
TI - Unexpected formation of 4-hydroxy-6-nitroindoles in the intramolecular cyclization of O-(3-amino-5-nitrophenyl)ketoximes
T2 - Mendeleev Communications
AU - Vorob'ev, Sergei Sergeyevich
AU - Dutov, Mikhail Dmitrievich
AU - Vatsadze, Irina Anatol'evna
AU - Kachala, Vadim Vadimovich
AU - Strelenko, Yurii Andreevich
AU - Sedov, Andrei A
AU - Shevelev, Svyatoslav Arkad'evich
PY - 2007
DA - 2007/03/15
PB - Mendeleev Communications
SP - 128-129
IS - 2
VL - 17
ER -
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@article{2007_Vorob'ev,
author = {Sergei Sergeyevich Vorob'ev and Mikhail Dmitrievich Dutov and Irina Anatol'evna Vatsadze and Vadim Vadimovich Kachala and Yurii Andreevich Strelenko and Andrei A Sedov and Svyatoslav Arkad'evich Shevelev},
title = {Unexpected formation of 4-hydroxy-6-nitroindoles in the intramolecular cyclization of O-(3-amino-5-nitrophenyl)ketoximes},
journal = {Mendeleev Communications},
year = {2007},
volume = {17},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.03.026},
number = {2},
pages = {128--129},
doi = {10.1016/j.mencom.2007.03.026}
}
MLA
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Vorob'ev, Sergei Sergeyevich, et al. “Unexpected formation of 4-hydroxy-6-nitroindoles in the intramolecular cyclization of O-(3-amino-5-nitrophenyl)ketoximes.” Mendeleev Communications, vol. 17, no. 2, Mar. 2007, pp. 128-129. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.03.026.

Abstract

The acid-catalysed cyclization of O-(3-amino-5-nitrophenyl)ketoximes unexpectedly gives, along with 6-amino-4-nitrobenzofurans, 4-hydroxy-6-nitroindoles (in a 1:1 ratio).

References

1.
Dutov M.D., Vatsadze I.A., Vorob’ev S.S., Shevelev S.A.
Mendeleev Communications, 2005
3.
Preparation of 8-Amido-2-dimethylamino-1,2,3,4-tetrahydro-2-dibenzofurans and Several Fluorinated Derivatives via [3,3]-Sigmatropic Rearrangement of O-Aryloximes
Guzzo P.R., Buckle R.N., Chou M., Dinn S.R., Flaugh M.E., Kiefer, A.D., Ryter K.T., Sampognaro A.J., Tregay S.W., Xu Y.
Journal of Organic Chemistry, 2003