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Naphthacenequinones: synthesis and properties

Nataliya Timofeevna Sokolyuk 1
Nataliya Timofeevna Sokolyuk
, 
V V Romanov 2
V V Romanov
, 
Lyudmila Pavlovna Pisulina 3
Lyudmila Pavlovna Pisulina
1 Research Institute of Fine Organic Synthesis of the 'TOS Industrial Association' Joint-Stock Company, Moscow Region
2 Production Association "ANILIN", Stavropol
3 Institute of Solution Chemistry of the Russian Academy of Sciences, Ivanovo
Published 30 November 1992
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Sokolyuk N. T., Romanov V. V., Pisulina L. P. Naphthacenequinones: synthesis and properties // Russian Chemical Reviews. 1993. Vol. 62. No. 11. pp. 1005-1024.
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Sokolyuk N. T., Romanov V. V., Pisulina L. P. Naphthacenequinones: synthesis and properties // Russian Chemical Reviews. 1993. Vol. 62. No. 11. pp. 1005-1024.
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TY - JOUR
DO - 10.1070/RC1993v062n11ABEH000061
UR - https://rcr.colab.ws/publications/10.1070/RC1993v062n11ABEH000061
TI - Naphthacenequinones: synthesis and properties
T2 - Russian Chemical Reviews
AU - Sokolyuk, Nataliya Timofeevna
AU - Romanov, V V
AU - Pisulina, Lyudmila Pavlovna
PY - 1993
DA - 1992/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 1005-1024
IS - 11
VL - 62
ER -
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@article{1993_Sokolyuk,
author = {Nataliya Timofeevna Sokolyuk and V V Romanov and Lyudmila Pavlovna Pisulina},
title = {Naphthacenequinones: synthesis and properties},
journal = {Russian Chemical Reviews},
year = {1993},
volume = {62},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1993v062n11ABEH000061},
number = {11},
pages = {1005--1024},
doi = {10.1070/RC1993v062n11ABEH000061}
}
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Sokolyuk, Nataliya Timofeevna, et al. “Naphthacenequinones: synthesis and properties.” Russian Chemical Reviews, vol. 62, no. 11, Nov. 1993, pp. 1005-1024. https://rcr.colab.ws/publications/10.1070/RC1993v062n11ABEH000061.
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Abstract

The literature data on the methods of synthesis and the properties of naphthacenequinones and related compounds are surveyed. The tautomeric and photochromic transformations of naphthacenequinone derivatives are examined. The bibliography includes 158 references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. , 1956
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) , 1952
4.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1953
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
7.
7
E. Rabinowitch
"Photosynthesis" , 1956
8.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959
9.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
10.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
11.
11
T. T. Bannister
Diss. Abstr. , 1959
12.
12
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
13.
13
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
14.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
15.
15
A. S. Holt
"Research in Photosynthesis" , 1957
16.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
17.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
19.
19
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1959
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
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.
Zur Konstitution des ?- und ?-Rhodomycinons
Brockmann H., Niemeyer J.
Die Naturwissenschaften , 1961
35.
35
Z. K. Maizus
Dokl. Akad. Nauk SSSR , 1960
37.
Chemistry of quinones. Part 7. Synthesis of anthracyclinone analogues via Diels–Alder reactions of 1,4-anthraquinones
Gupta D.N., Hodge P., Khan N.
Journal of the Chemical Society Perkin Transactions 1 , 1981
38.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
39.
39
V. F. Gachkovskii
Biofizika , 1959
41.
41
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1950
43.
43
N. Bunge
Ber. Deutsch. Chem. Ges. , 1870
44.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
45.
Regio- and stereo-selective construction of anthracyclinones: total synthesis of (–)-γ-rhodomycinone
Fujioka H., Yamamoto H., Kondo H., Annoura H., Kita Y.
Journal of the Chemical Society Chemical Communications , 1989
46.
46
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1955
47.
47
G. Oster
"Research in Photosynthesis" , 1957
48.
48
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
49.
49
A. A. Krasnovskii
Biofizika , 1958
50.
305. Homologues of naphthacene. Part I. 2 : 6-Dimethylnaphthacene
Coulson E.A.
Journal of the Chemical Society (Resumed) , 1934
51.
306. β-isoPropylnaphthacene
Cook J.W.
Journal of the Chemical Society (Resumed) , 1934
52.
Further Observations on the Use of Hydrogen Fluoride in Acylations and Cyclizations
Fieser L.F., Hershberg E.B.
Journal of the American Chemical Society , 1940
53.
53
D. Porretand E. Rabinowitch
Nature , 1937
54.
54
R. Livingston
J. Phys. Chem. , 1941
55.
752. The ozonolysis of polycyclic hydrocarbons. Part III
Copeland P.G., Dean R.E., McNeil D.
Journal of the Chemical Society (Resumed) , 1961
56.
645. The oxidation of some higher aromatic hydrocarbons with perbenzoic acid
Roitt I.M., Waters W.A.
Journal of the Chemical Society (Resumed) , 1949
57.
57
R. Livingston
"Research in Photosynthesis" , 1957
58.
Umwandlungen des Aethindiphtalids. II
Gabriel S., Leupold E.
Berichte der deutschen chemischen Gesellschaft , 1898
59.
59
H. Linshitz
"Research in Photosynthesis" , 1957
60.
60
A. N. Terenin
Optika i Spektrosk. , 1956
61.
61
A. N. Terenin
1959
62.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
63.
63
1930
64.
64
Chem. Zentr. II , 1931
65.
65
A. A. Krasnovskii
Biofizika , 1959
66.
Über einen neuen Aufbau in der lin. Benzanthrachinon‐Reihe
Waldmann H., Mathiowetz H.
Berichte der deutschen chemischen Gesellschaft (A and B Series) , 1931
67.
324. Grignard reactions with phthalic anhydrides
Weizmann C., Bergmann E., Bergmann F.
Journal of the Chemical Society (Resumed) , 1935
68.
Studien und Synthesen in der Reihe des Naphtacenchinons
Deichler C., Weizmann C.
Berichte der deutschen chemischen Gesellschaft , 1903
69.
88. The boric acid synthesis of peri-hydroxyanthraquinones
Weizmann C., Haskelberg L., Berlin T.
Journal of the Chemical Society (Resumed) , 1939
70.
Hydroxy‐tetracenchinone
Brockmann H., Müller W.
Chemische Berichte , 1959
71.
Synthesis of potential anticancer agents. 5,12-Naphthacene-quinones
Finkelstein J., Romano J.A.
Journal of Medicinal Chemistry , 1970
72.
XXXV.—Derivatives of naphthacenequinone. Part III
Harrop D., Norris R.V., Weizmann C.
Journal of the Chemical Society Transactions , 1909
73.
XLII.—Derivatives of naphthacenequinone
Bentley W.H., Friedl A., Thomas F., Weizmann C.
Journal of the Chemical Society Transactions , 1907
74.
Über lin. Benzanthrachinone
Waldmann H., Polak G.
Journal für praktische Chemie , 1938
75.
Was ist Osborne'sche Diastase?
Wróblewski A.
Berichte der deutschen chemischen Gesellschaft , 1898
76.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) , 1947
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
82.
82
G. P. Brin
Biokhimiya , 1957
83.
83
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
84.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
85.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
86.
86
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
87.
87
J. F. Arens
"Advances in Organic Chemistry" , 1960
88.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1946
89.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow , 1955
90.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1951
91.
91
L. M. Vorob'eva
Biokhimiya , 1956
92.
Beitrag zur Synthese von Tetracenchinonen
Winkler R.E.
Helvetica Chimica Acta , 1967
93.
Antitumor activity of some derivatives of daunorubicin at the amino and methyl ketone functions
Yamamoto K., Acton E.M., Henry D.W.
Journal of Medicinal Chemistry , 1972
94.
94
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
97.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR , 1952
98.
Quinizarin boroacetate and 1,4-diaminoanthraquinone diboroacetate as dienophiles
Birch A.M., Mercer A.J., Chippendale A.M., Greenhalgh C.W.
Journal of the Chemical Society Chemical Communications , 1977
101.
Studies on the syntheses of tetracycline derivatives. I. Thermolytic cycloaddition of o-quinodimethanes with naphthoquinone.
KAMETANI T., TAKAHASHI T., KAJIWARA M., HIRAI Y., OHTSUKA C., SATOH F., FUKUMOTO K.
Chemical and Pharmaceutical Bulletin , 2011
102.
102
F. Fichter
Helv. Chim. Acta , 1922
103.
Synthesis of polyacenequinones a benzo[2,3-c]furan
105.
Regioselective synthesis of substituted rubrenes
Dodge J.A., Bain J.D., Chamberlin A.R.
Journal of Organic Chemistry , 1990
106.
106
F. Fichter
Helv. Chim. Acta , 1927
107.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
108.
Notizen: Die Darstellung von Naphthacenchinonen aus Diels-Alder-Verbindungen des p-Benzochinons.
Lange W.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences , 1976
109.
109
F. Ficher
Bull. Soc. chim. France (4) , 1916
110.
110
M. F. Shostakovskii
Dokl. Akad. Nauk SSSR , 1960
111.
111
M. Calvin
1956
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
119.
Experiments on the synthesis of tetracycline. Part XIV. Closure of ring B by base-catalysed photocyclisation
Barton D.H., Bateson J.H., Datta S.C., Magnus P.D.
Journal of the Chemical Society Perkin Transactions 1 , 1976
120.
120
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
121.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
123.
123
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
124.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
125.
125
K. A. Andrianov
Vysokomol. Soed. , 1960
126.
126
J. Wiemannand Ch. Clachet
Compt. rend. , 1948
127.
127
R. Pasternak
Helv. Chim. Acta , 1948
128.
128
J. Wiemann
Bull. Soc. chim. France , 1952
129.
Über ms-Benzacridan-Abkömmlinge
Waldmann H., Hindenburg K.
Journal für praktische Chemie , 1940
130.
130
J. Wiemann
Bull. Soc. chim. France , 1958
131.
131
N. Thooi
Compt. rend. , 1958
132.
132
G. Shima
Kyoto Univ. , 1929
133.
Experiments on the synthesis of tetracycline. Part III. Michael-type cyclisation in the formation of ring B
Aufderhaar E., Baldwin J.E., Barton D.H., Faulkner D.J., Slaytor M.
Journal of the Chemical Society C Organic , 1971
134.
134
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1948
135.
Experiments of the synthesis of tetracycline. Part V. Photocyclisation of ring B
Barton D.H., Clive D.L., Magnus P.D., Smith G.
Journal of the Chemical Society C Organic , 1971
136.
REDUCTION PRODUCTS OF NAPHTHACENEQUINONE
Fieser L.F.
Journal of the American Chemical Society , 1931
137.
137
S. R. Rafikov
Zh. Obshch. Khim. , 1944
138.
138
S. Ono
J. Chem. Soc. Japan , 1957
139.
139
I. L. Knunyants
1959
140.
140
1912
141.
Reduction polarographique de quinones dans les solvants mixtes eau-pyridine
Brisset J.
Journal of Electroanalytical Chemistry and Interfacial Electrochemistry , 1975
142.
Nepraš M., Kratochvíl V., Titz M., Novák A., Slavík V.
Collection of Czechoslovak Chemical Communications , 2012
143.
145.
Effect of Molecular Size on the Association ofp-Quinone Anion and Lithium Ion inN,N-Dimethylformamide
Nagaoka T., Okazaki S., Fujinaga T.
Bulletin of the Chemical Society of Japan , 1982
147.
147
Y. Sasada
Acta Cryst. , 1898
148.
148
P. Kresse
Chem. Abs. , 1960
149.
149
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1954
150.
150
Ya. E. Bernadskaya
"Iskusstvennoe Volokno" (Artificial Fibres) , 1952
151.
151
V. M. Rodionov
Zhur. Obshch. Khim. , 1936
152.
152
W. Albert
Trans. Electrochem. Soc. , 1943
154.
154
Friedl.
155.
155
M. V. Mal'tsev
Izv. Vys. Ucheb. Zaved., Tsvet. Met. , 1960
156.
156
J. S. Fruton
J. Biol. Med. , 1950
157.
157
1903
159.
159
J. Tafel
Z. Elektrochem. , 1911
160.
160
1912
161.
161
Friedl.
162.
162
1917
163.
163
Friedl.
164.
164
1917
165.
Zur Kenntnis der Reaktivität polycyclischer Chinone. 2. Mitteilung
166.
Novák A., Titz M., Nepraš M.
Collection of Czechoslovak Chemical Communications , 2012
167.
167
Friedl.
168.
168
1918
169.
Nepraš M., Novák A.
Collection of Czechoslovak Chemical Communications , 2012
170.
170
1918
171.
171
Friedl.
172.
Synthetic Studies on Anthracyclinones. XIII. Conversion of Bisanhydro-γ-rhodomycinone into Bisanhydrodaunomycinone
HORII Z., OZAKI Y., YAMAMURA S., NISHIKADO T., HANAOKA M., MOMOSE T.
Chemical and Pharmaceutical Bulletin , 2011
173.
173
Friedl.
174.
174
S. Calvert
India Rubber Tire Rev. , 1926
175.
175
I. Mayer
1966
176.
Die Dibenzalbernsteinsäure. (III. Abhandlung über Butadiënverbindungen.)
Stobbe H., Naoúm P.
Berichte der deutschen chemischen Gesellschaft , 1904
177.
177
J. Henry
Proc. R. Irish Acad. , 1945
178.
178
1946
179.
179
Chem. Abs. , 1947
180.
180
1946
181.
181
Chem. Abs. , 1947
182.
182
1947
183.
183
Chem. Abs. , 1947