Home / Articles / Azafluorenes. Synthesis and conversions

Azafluorenes. Synthesis and conversions

Nikolai Sergeevich Prostakov 1
Nikolai Sergeevich Prostakov
, 
Anatoly Timofeevich Soldatenkov 1
Anatoly Timofeevich Soldatenkov
, 
Nadezhda Mikhailovna Kolyadina 1
Nadezhda Mikhailovna Kolyadina
, 
Arnol'd Aleksandrovich Obynochnyi 1
Arnol'd Aleksandrovich Obynochnyi
1 Peoples Friendship University of Russia, Moscow
10.1070/RC1997v066n02ABEH000263
Published 30 November 1996
Communication , Volume 66, Issue 2, 121-138
15
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Prostakov N. S. et al. Azafluorenes. Synthesis and conversions // Russian Chemical Reviews. 1997. Vol. 66. No. 2. pp. 121-138.
GOST all authors (up to 50)
Copy cite
Prostakov N. S., Soldatenkov A. T., Kolyadina N. M., Obynochnyi A. A. Azafluorenes. Synthesis and conversions // Russian Chemical Reviews. 1997. Vol. 66. No. 2. pp. 121-138.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RC1997v066n02ABEH000263
UR - https://rcr.colab.ws/publications/10.1070/RC1997v066n02ABEH000263
TI - Azafluorenes. Synthesis and conversions
T2 - Russian Chemical Reviews
AU - Prostakov, Nikolai Sergeevich
AU - Soldatenkov, Anatoly Timofeevich
AU - Kolyadina, Nadezhda Mikhailovna
AU - Obynochnyi, Arnol'd Aleksandrovich
PY - 1997
DA - 1996/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 121-138
IS - 2
VL - 66
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{1997_Prostakov,
author = {Nikolai Sergeevich Prostakov and Anatoly Timofeevich Soldatenkov and Nadezhda Mikhailovna Kolyadina and Arnol'd Aleksandrovich Obynochnyi},
title = {Azafluorenes. Synthesis and conversions},
journal = {Russian Chemical Reviews},
year = {1997},
volume = {66},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1997v066n02ABEH000263},
number = {2},
pages = {121--138},
doi = {10.1070/RC1997v066n02ABEH000263}
}
MLA
Cite this
MLA
Copy cite
Prostakov, Nikolai Sergeevich, et al. “Azafluorenes. Synthesis and conversions.” Russian Chemical Reviews, vol. 66, no. 2, Nov. 1997, pp. 121-138. https://rcr.colab.ws/publications/10.1070/RC1997v066n02ABEH000263.
Views / Visits / Downloads
22 / 22 / 30

Abstract

Data on the chemistry of azafluorenes (indenopyridines) for the last two decades are summarised. Methods of synthesis of all isomeric (as regards the position of the nitrogen atom) azafluorenes are considered. The main reactions of azafluorenes are analysed, their reactivity is determined by the presence and mutual influence of two different conjugated fused rings (benzene and pyridine) and the mode of fusion of the indene and pyridine fragments. The principal conversions of substituents at different positions of the azafluorene system are considered. Evidence is presented on the natural occurrence of azafluorenes, the biological activity of their synthetic derivatives, and on the structure and physicochemical properties of azafluorenes and their derivatives. The bibliography includes 204 references.

References

1.
Benzoisoquinolines and Azafluorenes
Prostakov N.S.
Russian Chemical Reviews , 1969
2.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) , 1952
4.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1953
6.
7
E. Rabinowitch
"Photosynthesis" , 1956
7.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959
8.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
9.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
10.
High resolution13C and1H NMR spectral analysis of 1-azafluorene
Fomichov A.A., Svoren V.A., Golovtsov N.I., Soldatenkov A.T., Prostakov N.S.
Magnetic Resonance in Chemistry , 1982
11.
Analysis of1H NMR spectra of fluorene and azafluorenes: Long-range coupling constants
Fomichov A.A., Lawani-Edogiawerie S.O., Prostakov N.S.
Magnetic Resonance in Chemistry , 1983
12.
13C-NMR Spectra of Azafluorenones
Cassels B.K., Tadic´ D., Laprévote O., Cavé A.
Journal of Natural Products , 1989
13.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
14.
15
A. S. Holt
"Research in Photosynthesis" , 1957
15.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
16.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
17.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
18.
19
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1959
19.
20
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
20.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
21.
22
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
22.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR , 1958
23.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR , 1951
24.
25
G. W. Robinson
J. Chem. Phys. , 1955
25.
26
B. Ya. Dain
1957
26.
27
A. A. Krasnovskii
Biofizika , 1956
27.
28
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
28.
29
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
29.
Onychine, an alkaloid from Onychopetalum amazonicum☆
De Almeida M.E., Braz F R., von Bülow V., Gottlieb O.R., Maia J.G.
Phytochemistry , 1976
30.
A New Method for Constructing Pyridine Ring: Thermolysis of Oxime O-Alyly Ether
Koyama J., Suzuta Y., Irie H., Katayama I.
Heterocycles , 1979
31.
32
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
32.
Anticandidal Activity of Eupolauridine and Onychine, Alkaloids from Cleistopholis patens
Hufford C.D., Liu S., Clark A.M., Oguntimein B.O.
Journal of Natural Products , 1987
33.
Azafluorenones and azaanthraquinone from Guatteria dielsiana
Goulart M.O., Santana A.E., De Oliveira A.B., De Oliveira G.G., Maia J.G.
Phytochemistry , 1986
34.
Revised structures of the azafluorenone alkaloids from guateria dielsiana
Tadić D., Cassels B.K., Cavé A., Goulart M.O., De Oliveira A.B.
Phytochemistry , 1987
36.
Geovanine, a new azaanthracene alkaloid from Annona ambotay aubl.☆☆☆
B. De Oliveira A., G. De Oliveira G., Carazza F., Guilherme S. Maia J.
Phytochemistry , 1987
37.
Azafluorenones from Oxandra cf. major and biogenetic considerations
Mérienne C., Arango G.J., Cortes D., Cassels B.K., Cavé A.
Phytochemistry , 1987
38.
Two New Natural Azafluorene Alkaloids and a Cytotoxic Aporphine Alkaloid from Polyalthia longifolia
Wu Y., Duh C., Wang S., Chen K., Yang T.
Journal of Natural Products , 1990
39.
40
A. A. Krasnovskii
Biofizika , 1960
40.
41
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1950
44.
Aporphinoid Alkaloids, IV
Guinaudeau H., Leboeuf M., Cavé A.
Journal of Natural Products , 1988
48.
49
A. A. Krasnovskii
Biofizika , 1958
50.
51
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
51.
Über die Basen des Steinkohlenteer‐Pechs
Oberkobusch R.
Chemische Berichte , 1953
52.
53
D. Porretand E. Rabinowitch
Nature , 1937
53.
Synthesis of Azafluorenones
Kloc K., Mlochowski J., Szulc Z.
Journal für praktische Chemie , 1977
54.
453. New syntheses of heterocyclic compounds. Part X. 4-Azafluorenones
Petrow V., Saper J., Sturgeon B.
Journal of the Chemical Society (Resumed) , 1949
55.
56
T. Iasui
Bull. Chem. Soc. Japan. , 1935
56.
57
R. Livingston
"Research in Photosynthesis" , 1957
57.
58
N. E. Khomutov
1953
58.
59
H. Linshitz
"Research in Photosynthesis" , 1957
59.
60
A. N. Terenin
Optika i Spektrosk. , 1956
60.
61
A. N. Terenin
1959
61.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
62.
63
1930
64.
65
A. A. Krasnovskii
Biofizika , 1959
65.
66
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
66.
67
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1940
68.
69
B. Commoner
1958
69.
70
N. Bubnov
Biofizika , 1960
72.
Synthesis of 3,9-dihydro-3,9-dioxo-2H-indeno[2,1-c] pyridine-4-carbonitriles
Chorvat R.J., Desai B.N.
Journal of Heterocyclic Chemistry , 1980
75.
Heterocyclen aus Enaminonen
Möhrle H., Novak H.
Archiv der Pharmazie , 1982
76.
77
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
80.
Synthesis and some reactions of ketonic mannich bases related to 1,3-Indandione
Afsah E.M., Hassan H.M., El-Agizy S.A., Zimaity M.T.
Journal für praktische Chemie , 1984
82.
83
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
83.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
84.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
86.
87
J. F. Arens
"Advances in Organic Chemistry" , 1960
87.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1946
88.
Synthesis of Several 2-Azafluorenones and 5H[1]Benzopyrano[3,4-c]Py Riding-Ones
Shiao M., Peng C., Wang J., Ma Y.
Journal of the Chinese Chemical Society , 1992
89.
Pyridindene Derivatives. III. Synthesis from Arecoline
PLATI J.T., INGBERMAN A.K., WENNER W.
Journal of Organic Chemistry , 1957
90.
Total synthesis of the diazaphenanthrene alkaloid perlolidine
Powers J.C., Ponticello I.
Journal of the American Chemical Society , 1968
92.
A facile synthesis of 7-halo-5H-indeno[1,2-b]pyridines and -pyridin-5-ones
DuPriest M.T., Schmidt C.L., Kuzmich D., Williams S.B.
Journal of Organic Chemistry , 1986
93.
94
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
94.
95
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
95.
96
L. M. Vorob'eva
Biokhimiya , 1958
96.
The interaction of 2,6-dimethyl-3,5-dicarboxy-4-phenylpyridine with SF4 in HF solution
Yagupolskii L.M., Petko K.I., Retchitsky A.N., Maletina I.I.
Journal of Fluorine Chemistry , 1994
97.
The Condensation of Grignard Reagents with 3-Pyridyl and 3-Quinolyl Ketones
Fuson R.C., Miller J.J.
Journal of the American Chemical Society , 1957
98.
99
V. V. Zolotarev
1938
99.
PYRIDINDENE DERIVATIVES. I
PLATI J.T., WENNER W.
Journal of Organic Chemistry , 1950
100.
101
M. F. Shostakovskii
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
101.
Pyridindene Derivatives. IV. Alkylated Pyridindenes
PLATI J.T., WENNER W.
Journal of Organic Chemistry , 1960
103.
104
O. P. Osipova
Dokl. Akad. Nauk SSSR , 1950
104.
AROMATIC SUBSTITUTION: PART IX. ON THE MECHANISM OF THE PSCHORR CYCLIZATION
Abramovitch R.A., Tertzakian G.
Canadian Journal of Chemistry , 1965
105.
A general synthesis of substituted fluorenones and azafluorenones
Kyba E.P., Liu S.T., Chockalingam K., Reddy B.R.
Journal of Organic Chemistry , 1988
106.
Intramolecular cyclization of nitrile imines. Synthesis of indazoles, fluorenes, and aza analogs
Wentrup C., Damerius A., Reichen W.
Journal of Organic Chemistry , 1978
108.
109
F. Ficher
Bull. Soc. chim. France (4) , 1916
109.
110
M. F. Shostakovskii
Dokl. Akad. Nauk SSSR , 1960
110.
111
M. Calvin
1956
111.
112
A. G. Pozdeeva
Zhur. Prikl. Khim. , 1952
112.
113
H. Blum
"Photodynamic Action and Diseases caused Light" , 1940
113.
114
L. Segal
"Chemical Reactions of Polymers" , 1964
114.
115
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1957
115.
116
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
116.
117
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
117.
118
V. M. Rodionov
Zhur. Obshch. Khim. , 1935
118.
119
V. V. Levchenko
Zhur. Obshch. Khim. , 1947
119.
120
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
120.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
121.
122
S. R. Rafikov
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
122.
123
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
123.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
124.
125
K. A. Andrianov
Vysokomol. Soed. , 1960
125.
Indenyl and fluorenyl transition metal complexes
Thoma T., Pleshakov V.G., Prostakov N.S., Ustynyuk Y.A., Nesmeyanov A.N., Ustynyuk N.A.
Journal of Organometallic Chemistry , 1980
126.
Indenyl and fluorenyl transition metal complexes
Nesmeyanov A.N., Ustynyuk N.A., Thoma T., Prostakov N.S., Soldatenkov A.T., Pleshakov V.G., Urga K., Ustynyuk Y.A., Trifonova O.I., Oprunenko Y.F.
Journal of Organometallic Chemistry , 1982
127.
Reactions at the nitrogen atoms in azafluorene systems
Kloc K., Młochowski J., Szulc Z.
Canadian Journal of Chemistry , 1979
128.
129
J. Wiemann
Bull. Soc. chim. France , 1955
129.
130
J. Wiemann
Bull. Soc. chim. France , 1958
130.
131
N. Thooi
Compt. rend. , 1958
131.
132
G. Shima
Kyoto Univ. , 1929
132.
133
C. Wilson
Trans. Electrochem. Soc. , 1941
133.
134
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1948
134.
Novel pharmacological activity of a series of substituted pyridines
Butler D.E., Bass P., Nordin I.C., Hauck F.P., L'Italien Y.J.
Journal of Medicinal Chemistry , 1971
135.
136
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1954
136.
137
S. R. Rafikov
Zh. Obshch. Khim. , 1944
137.
138
S. Ono
J. Chem. Soc. Japan , 1957
138.
139
I. L. Knunyants
1959
139.
140
1912
140.
141
Friedl.
141.
142
1913
142.
143
Friedl.
143.
144
1912
144.
145
Friedl.
145.
146
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1952
146.
147
Y. Sasada
Acta Cryst. , 1898
147.
148
P. Kresse
Chem. Abs. , 1960
148.
149
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1954
149.
150
Ya. E. Bernadskaya
"Iskusstvennoe Volokno" (Artificial Fibres) , 1952
150.
151
V. M. Rodionov
Zhur. Obshch. Khim. , 1936
151.
152
W. Albert
Trans. Electrochem. Soc. , 1943
153.
154
Friedl.
154.
155
M. V. Mal'tsev
Izv. Vys. Ucheb. Zaved., Tsvet. Met. , 1960
155.
156
J. S. Fruton
J. Biol. Med. , 1950
156.
157
1903
157.
158
Friedl.
158.
159
J. Tafel
Z. Elektrochem. , 1911
159.
160
1912
160.
161
Friedl.
161.
162
1917
162.
163
Friedl.
163.
164
1917
164.
165
Friedl.
165.
Jacquignon P., Perin-Roussel O.
Collection of Czechoslovak Chemical Communications , 2012
166.
167
Friedl.
167.
168
1918
168.
169
Friedl.
169.
170
1918
170.
171
Friedl.
171.
172
1918
172.
173
Friedl.
173.
174
S. Calvert
India Rubber Tire Rev. , 1926
174.
175
I. Mayer
1966
175.
176
G. V. Samsonov
"Metody Ispytaniya na Mikrotverdost' i Pribory" (Methods of Microhardness Testing and Apparatus) , 1965
176.
177
J. Henry
Proc. R. Irish Acad. , 1945
177.
178
1946
178.
179
Chem. Abs. , 1947
179.
180
1946
180.
181
Chem. Abs. , 1947
181.
182
1947
182.
183
Chem. Abs. , 1947
183.
184
F. Haurowitz
"The Chemistry and Function of Proteins" , 1965
184.
185
1954
185.
186
Chem. Abs. , 1956
186.
Phosphonic Derivatives of Azafluorenes
Wieczorek J.S., Boduszek B., Gancarz R.
Journal für praktische Chemie , 1984
187.
The Reduction of Azafluorenones
Mlochowski J., Kloc K., Szulc Z.
Heterocycles , 1978
188.
189
M. Godchot
Bull. Soc. chim. France (5) , 1913
189.
190
H. Law
J. Chem. Soc. , 1912
190.
Darstellung von 2H-cyclopent[j.k]Fluoren und substituierten fluoradenen
Tuchscherer C., Bruch M., Rewicki D.
Tetrahedron Letters , 1973
191.
192
E. Pannain
Rend. Classe Sci. fis. mat. nat. (5) , 1908
192.
193
E. Pannain
Gazzetta , 1909
193.
194
A. A. Vertman
"Svoistva Rasplavov Zheleza" (Properties of Iron Melts) , 1969
194.
195
M. Allen
J. Chem. Soc. , 1961
195.
196
E. Müller
Z. Elektrochem. , 1910
196.
197
J. Sicher
Chem. Listy , 1955
197.
198
W. Cohen
Rec. Trav. chim. , 1919
198.
199
Yu. K. Delimarskii
Byull. Izobr. , 1970
201.
202
G. Shiroa
Mem. Coll. Sci., Kyoto Univ. , 1930
202.
Studies on Inhibitors of Skin Tumor Promotion, VI. Inhibitory Effects of Quinones on Epsterin-Barr Virus Activation
Konoshima T., Kozuka M., Koyama J., Tagahara T.O., Tokuda H.
Journal of Natural Products , 1989
203.
204
Cherkesov A I
Ref. Zh. Khim. , 1968
204.
205
N. Bunge
Zhur. Russ. Fiz.-Khim. Obshch. , 1889
205.
206
J. Petersen
Z. Phys. Chem. , 1900