Home / Articles / 1,2,4-Triazine N-oxides and their annelated derivatives

1,2,4-Triazine N-oxides and their annelated derivatives

Dmitry Nikolaevich Kozhevnikov 1
Dmitry Nikolaevich Kozhevnikov
,  , 
Oleg Nikolaevich Chupakhin 1
Oleg Nikolaevich Chupakhin
1 Ural State Technical University, Ekaterinburg
Published 30 November 1997
Communication , Volume 67, Issue 8, 633-648
28
Share
Cite this
GOST
 | 
Cite this
GOST
Kozhevnikov D. N., Rusinov V. L., Chupakhin O. N. 1,2,4-Triazine N-oxides and their annelated derivatives // Russian Chemical Reviews. 1998. Vol. 67. No. 8. pp. 633-648.
GOST all authors (up to 50)
Kozhevnikov D. N., Rusinov V. L., Chupakhin O. N. 1,2,4-Triazine N-oxides and their annelated derivatives // Russian Chemical Reviews. 1998. Vol. 67. No. 8. pp. 633-648.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RC1998v067n08ABEH000437
UR - https://rcr.colab.ws/publications/10.1070/RC1998v067n08ABEH000437
TI - 1,2,4-Triazine N-oxides and their annelated derivatives
T2 - Russian Chemical Reviews
AU - Kozhevnikov, Dmitry Nikolaevich
AU - Rusinov, Vladimir Leonidovich
AU - Chupakhin, Oleg Nikolaevich
PY - 1998
DA - 1997/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 633-648
IS - 8
VL - 67
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{1998_Kozhevnikov,
author = {Dmitry Nikolaevich Kozhevnikov and Vladimir Leonidovich Rusinov and Oleg Nikolaevich Chupakhin},
title = {1,2,4-Triazine N-oxides and their annelated derivatives},
journal = {Russian Chemical Reviews},
year = {1998},
volume = {67},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1998v067n08ABEH000437},
number = {8},
pages = {633--648},
doi = {10.1070/RC1998v067n08ABEH000437}
}
MLA
Cite this
MLA
Kozhevnikov, Dmitry Nikolaevich, et al. “1,2,4-Triazine N-oxides and their annelated derivatives.” Russian Chemical Reviews, vol. 67, no. 8, Nov. 1998, pp. 633-648. https://rcr.colab.ws/publications/10.1070/RC1998v067n08ABEH000437.
Views / Visits / Downloads
18 / 18 / 3

Abstract

This review deals with the synthesis and properties of 1,2,4-triazine N-oxides and their annelated derivatives. Methods for the incorporation of the N-oxide group in the 1,2,4-triazine ring by direct oxidation and cyclisation involving nitro, nitroso, and isonitroso groups are discussed. Reactions of 1,2,4-triazine N-oxides with electrophiles, nucleophiles, and dienophiles are considered. The effect of the N-oxide group on the chemical shifts in the 1H, 13C, and 14N NMR spectra and the specific features of decomposition of 1,2,4-triazine N-oxides under electron impact are analysed. The bibliography includes 107 references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
Pyrimidine N-Oxides: Syntheses, Structures, and Chemical Properties
Yamanaka H., Sakamoto T., Niitsuma S.
Heterocycles , 1990
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) , 1952
4.
Progress in the chemistry of quinoxalineN-oxides andN,N′-dioxides
Kurasawa Y., Takada A., Kim H.S.
Journal of Heterocyclic Chemistry , 1995
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
7.
7
E. Rabinowitch
"Photosynthesis" , 1956
8.
Behavior of Monocyclic 1,2,4-Triazines in Reactions with C-, N-, O-, and S-Nucleophiles
Charushin V.N., Alexeev S.G., Chupahkin O.N., Van Der Plas H.C.
Advances in Heterocyclic Chemistry , 1989
9.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
10.
Syntheses, carbon-13 and proton nuclear magnetic resonance spectra of some 1,2,4-triazine 1- and 2-oxides
Radel R.J., Keen B.T., Wong C., Paudler W.W.
Journal of Organic Chemistry , 1977
11.
Synthesis of 4-.beta.-D-ribofuranosyl-as-triazin-3(4H)-one 1-oxide a potential uridine antagonist
Szekeres G.L., Robins R.K., Dea P., Schweizer M.P., Long R.A.
Journal of Organic Chemistry , 1973
14.
1,2,4-Triazines. IV. Synthesis and characterization of 1,2,4-triazine N-oxides
15.
Synthesis of 6-Substituted 3,5-Diaryl-1,2,4-triazines as Potential Herbicidal Agents
Konno S., Osawa N., Yamanaka H., Sanemitsu Y., Kawamura S., Sakaki M.
Journal of Agricultural and Food Chemistry , 1995
16.
Condensed 1,2,4-triazines: synthesis of 5- benzyl-5H-imidazo[4,5-e]-1,2,4-triazine 1-oxides (9-benzyl-6-azapurine 6-oxides)
Tzeng C., Wei D., Hwang L., Cheng M., Wang Y.
Journal of the Chemical Society Perkin Transactions 1 , 1994
17.
Preparation of new 1,2,4-triazines
Repič O., Mattner P.G., Shapiro M.J.
Journal of Heterocyclic Chemistry , 1982
18.
623. Polyazabicyclic compounds. Part II. Further derivatives of benzo-1 : 2 : 4-triazine
Robbins R.F., Schofield K.
Journal of the Chemical Society (Resumed) , 1957
19.
Ringschluß zwischen Nitro- und Aminogruppe unter Bildung von Triazinen
Arndt F.
Berichte der deutschen chemischen Gesellschaft , 1913
20.
20
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
21.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
22.
22
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
23.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR , 1958
24.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR , 1951
25.
25
G. W. Robinson
J. Chem. Phys. , 1955
26.
26
B. Ya. Dain
1957
27.
27
A. A. Krasnovskii
Biofizika , 1956
28.
28
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
29.
29
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
30.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
31.
31
A. A. Krasnovskii
Biokhimiya , 1960
32.
Ring transformation of condensed dihydro-as-triazines
Berényi E., Benkó P., Zólyomi G., Tamás J.
Journal of Heterocyclic Chemistry , 1981
33.
33
M. B. Neiman
"Issledovanie Mekhanizma Okisleniya Butana" (Research on the Mechanism of the Oxidation of Butane) , 1939
34.
34
G. W. Robinson
J. Chem. Phys. , 1886
35.
35
Z. K. Maizus
Dokl. Akad. Nauk SSSR , 1960
36.
36
J. Billon
Bull. Soc. chim. France , 1960
37.
37
L. M. Kosobutskaya
Dokl. Akad. Nauk SSSR , 1950
40.
40
A. A. Krasnovskii
Biofizika , 1960
42.
Synthesis and antiinflammatory activity of trisubstituted pyrimidines and triazines
Bennett G.B., Mason R.B., Alden L.J., Roach J.B.
Journal of Medicinal Chemistry , 1978
43.
Carbon-13 NMR studies on 3-phenyl-as-triazine 4-oxides
Bennett G.B., Kahle A.D., Minor H., Shapiro M.J.
Journal of Heterocyclic Chemistry , 1979
45.
New Syntheses of Fervenulin 4-Oxides
Senga K., Ichiba M., Nishigaki S.
Heterocycles , 1977
46.
46
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1955
47.
Kozhevnikov Dmitry Nikolaevich, Kozhevnikov Valery Nikolaevich, Rusinov Vladimir Leonidovich, Chupakhin Oleg Nikolaevich
Mendeleev Communications , 1997
48.
New syntheses of alloxazine 5-oxides and fervenulin 4-osides by the nitrative cyclization.
SAKUMA Y., MATSUMOTO S., NAGAMATSU T., YONEDA F.
Chemical and Pharmaceutical Bulletin , 2011
49.
6-Azapurines (imidazo[4,5-e]-as-triazines)
Yoneda F., Nagamura T., Kawamura M.
Journal of the Chemical Society Chemical Communications , 1976
50.
A new synthesis of pyrimido[5,4-e]-as-triazine 4-oxides and their ring transformation to pyrrolo[3,2-d]pyrimidines
Nishigaki S., Kanazawa H., Kanamori Y., Ichiba M., Senga K.
Journal of Heterocyclic Chemistry , 1982
52.
Cyclization reactions of some 5-nitro- and 5-nitroso-6- benzylidenehydraziouracils.
YONEDA F., NAGAMATSU T.
Chemical and Pharmaceutical Bulletin , 2011
54.
54
R. Livingston
J. Phys. Chem. , 1941
55.
55
G. A. Bogdanovskii
1958
57.
57
R. Livingston
"Research in Photosynthesis" , 1957
58.
Oxides of 3-methyl-1,2,4-benzotriazine
Atallah R.H., Nazer M.Z.
Tetrahedron , 1982
59.
Reactions of benzofurazan oxide with amines—I
Nazer M.Z., Issidorides C.H., Haddadin M.J.
Tetrahedron , 1979
61.
61
A. N. Terenin
1959
62.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
63.
Bicycloaromaticity. Stability and rearrangement of the bicyclo[3.2.2]nonatrienyl cation
Grutzner J.B., Winstein S.
Journal of the American Chemical Society , 1970
65.
65
A. A. Krasnovskii
Biofizika , 1959
66.
66
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
68.
Localization ofN-oxide groups by means of nitrogen chemical shifts
Witanowski M., Stefaniak L., Kamieński B., Webb G.A.
Magnetic Resonance in Chemistry , 1980
69.
As-triazine chemistry—VI
Sasaki T., Minamoto K., Nishikawa M., Shima T.
Tetrahedron , 1969
70.
Mass spectra of some 3-amino-1,2,4-triazincsN-oxides
Paudler W.W., Chen T.
Journal of Heterocyclic Chemistry , 1971
71.
Brominations of some 1,2,4-triazine 2-oxides
Radel R.J., Atwood J.L., Paudler W.W.
Journal of Organic Chemistry , 1978
72.
3-Azido-1,2,4-triazineN-Oxides. Syntheses and structure elucidation
Goodman M.M., Paudler W.W.
Journal of Heterocyclic Chemistry , 1977
75.
75
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
76.
Intramolecular reaction between nitro and carbodi-imide groups; a new synthesis of 2-arylbenzotriazoles
Houghton P.G., Pipe D.F., Rees C.W.
Journal of the Chemical Society Perkin Transactions 1 , 1985
77.
77
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
78.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
79.
79
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
80.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1937
85.
Diazo-, azo-, and azidoazoles. VII. Imidazo[1,2-b]-versusimidazo[2,1-c]benzo-as-triazines
Castillón S., Meléndez E., Vilarrasa J.
Journal of Heterocyclic Chemistry , 1982
86.
Syntheses and characterization of some tetra- and pentaazaindene N-oxides
Paudler W.W., Sheets R.M.
Journal of Organic Chemistry , 1980
87.
87
J. F. Arens
"Advances in Organic Chemistry" , 1960
88.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1946
89.
1,2,4-Triazine 1- and 2-oxides. Reactivities toward some electrophiles and nucleophiles
Keen B.T., Radel R.J., Paudler W.W.
Journal of Organic Chemistry , 1977
91.
91
L. M. Vorob'eva
Biokhimiya , 1956
92.
92
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
93.
93
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
94.
94
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
95.
95
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
96.
96
L. M. Vorob'eva
Biokhimiya , 1958
97.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR , 1952
98.
98
W. Franke
Chem. Zentr. , 1954
99.
99
V. V. Zolotarev
1938
100.
100
V. V. Zolotarev
Chem. Abs. , 1941
101.
101
M. F. Shostakovskii
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
102.
102
F. Fichter
Helv. Chim. Acta , 1922
104.
Kozhevnikov Dmitry Nikolaevich, Ulomsky Eugeny Nartsissovich, Rusinov Vladimir Leonidovich, Chupakhin Oleg Nikolaevich, Neunhoeffer Hans
Mendeleev Communications , 1997
106.
106
F. Fichter
Helv. Chim. Acta , 1927
107.
Azev Yurii Alexeevich, Neunhoeffer Hans, Shorshnev Sergei Victorovich
Mendeleev Communications , 1996
108.
108
F. Fichter
Helv. Chim. Acta , 1924
109.
Reaction of 5,6-benzo-1,2,4-triazine 1-oxides with Grignard reagents
Igeta H., Nakai T., Tsuchiya T.
Journal of the Chemical Society Chemical Communications , 1973
110.
110
M. F. Shostakovskii
Dokl. Akad. Nauk SSSR , 1960
111.
111
M. Calvin
1956
112.
112
A. G. Pozdeeva
Zhur. Prikl. Khim. , 1952
113.
113
H. Blum
"Photodynamic Action and Diseases caused Light" , 1940
114.
114
L. Segal
"Chemical Reactions of Polymers" , 1964
115.
115
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1957