Abstract
Studies on the development of procedures for the synthesis of five isomeric pyridopyridines, viz., 1,5-, 1,6-, 1,7-, 2,6- and 2,7-naphthyridines, their chemical properties and biological activities performed over the last 15 years are surveyed and systematised. The bibliography includes 223 references.
References
1.
Litvinov V.P., Roman S.V., Dyachenko V.D.
Russian Chemical Reviews ,
2000
2.
Couture A., Deniau E., Grandclaudon P., Simion C.
Synthesis ,
1993
3.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1949
4.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1953
5.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1953
6.
7
E. Rabinowitch
"Photosynthesis" ,
1956
7.
Irikawa H., Okumura Y.
Bulletin of the Chemical Society of Japan ,
1987
8.
9
V. H. Lynch
Carnegie Inst. Year Book ,
1954
9.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) ,
1959
10.
Viti G., Giannotti D., Nannicini R., Balacco G., Pestellini V.
Tetrahedron Letters ,
1994
11.
12
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1950
12.
13
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1954
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.
Gronowitz S., Malm J., H嗷nfeldt A.
Heterocycles ,
1994
17.
Barlin G., Ireland S.
Australian Journal of Chemistry ,
1988
18.
Barlin G., Jiravinyu C.
Australian Journal of Chemistry ,
1990
19.
Barlin G., Jiravinyu C.
Australian Journal of Chemistry ,
1991
20.
Barlin G., Tan W.
Australian Journal of Chemistry ,
1985
21.
Barlin G., Tan W.
Australian Journal of Chemistry ,
1986
22.
Bawrlin G., Ireland S., Nguyen T., Kotecka B., Rieckmann K.
Australian Journal of Chemistry ,
1994
23.
Barlin G., Jiravinyu C., Yan J.
Australian Journal of Chemistry ,
1991
24.
Barlin G., Tan W.
Australian Journal of Chemistry ,
1985
25.
Barlin G., Tan W.
Australian Journal of Chemistry ,
1984
26.
Barlin G., Ireland S., Jiravinyu C., Nguyen T., Kotecka B., Rieckmann K.
Australian Journal of Chemistry ,
1993
27.
28
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1955
28.
29
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1951
29.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1954
30.
31
A. A. Krasnovskii
Biokhimiya ,
1960
31.
Woźniak M., Tomula M.
1993
32.
Castle R.N., Pakray S., Martin G.E.
Journal of Heterocyclic Chemistry ,
1991
33.
Achenbach H., Düthorn B., Waibel R.
1992
34.
35
Z. K. Maizus
Dokl. Akad. Nauk SSSR ,
1960
35.
36
J. Billon
Bull. Soc. chim. France ,
1960
36.
P. Cava M., A. Adesomoju A., V. Lakshmikantham M.
Heterocycles ,
1991
37.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1956
38.
39
V. F. Gachkovskii
Biofizika ,
1959
39.
40
A. A. Krasnovskii
Biofizika ,
1960
40.
41
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1950
41.
42
L. K. Obukhova
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk ,
1960
42.
43
N. Bunge
Ber. Deutsch. Chem. Ges. ,
1870
43.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1953
44.
45
W. Hendrich
Roczniki Chemii ,
1958
45.
46
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1955
46.
47
G. Oster
"Research in Photosynthesis" ,
1957
47.
Czibula L., Nemes A., Visky G., Farkas M., Szombathelyi Z., Kárpáti E., Sohár P., Kessel M., Kreidl J.
1993
48.
49
A. A. Krasnovskii
Biofizika ,
1958
49.
50
G. Glacomello
Gazzetta. ,
1935
50.
51
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1954
51.
52
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1957
52.
53
D. Porretand E. Rabinowitch
Nature ,
1937
53.
54
R. Livingston
J. Phys. Chem. ,
1941
54.
55
G. A. Bogdanovskii
1958
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
63.
64
Chem. Zentr. II ,
1931
64.
Singh B., Lesher G.Y.
Journal of Heterocyclic Chemistry ,
1990
65.
66.
67
N. N. Mel'nikov
Zhur. Obshch. Khim. ,
1940
67.
68
N. N. Mel'nikov
Zhur. Obshch. Khim. ,
1946
68.
69
B. Commoner
1958
69.
70
N. Bubnov
Biofizika ,
1960
70.
Balogh M., Hermecz I., Náray-Szabó G., Simon K., Mészáros Z.
Journal of the Chemical Society Perkin Transactions 1 ,
1986
71.
Balogh M., Hermecz I., Simon K., Pusztay L.
Journal of Heterocyclic Chemistry ,
2009
72.
Tóth G., Kovács A., Balogh M., Hermecz I.
Journal of Heterocyclic Chemistry ,
1991
73.
Kleinschroth J., Mannhardt K., Hartenstein J., Satzinger G.
Synthesis ,
1986
74.
75
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1950
75.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) ,
1947
76.
77
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1948
77.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1949
78.
79
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1952
79.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. ,
1937
80.
81
J. C. Ghosh
J. Indian Chem. Soc. ,
1934
81.
82
G. P. Brin
Biokhimiya ,
1957
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
85.
86
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1958
86.
87
J. F. Arens
"Advances in Organic Chemistry" ,
1960
87.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1946
88.
Singh B., Bacon E.R., Lesher G.Y., Robinson S., Pennock P.O., Bode D.C., Pagani E.D., Bentley R.G., Connell M.J., Hamel L.T., Silver P.J.
Journal of Medicinal Chemistry ,
1995
89.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1951
90.
91
L. M. Vorob'eva
Biokhimiya ,
1956
91.
92
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1948
92.
Erian A.W., Sherif S.M., Alassar A.A., Elkholy Y.M.
Tetrahedron ,
1994
93.
Nietsch K., Troschütz R., Roth H.J.
Archiv der Pharmazie ,
1985
94.
95
A. A. Krasnovskii
Fiziologiya Rastenii ,
1957
95.
96
L. M. Vorob'eva
Biokhimiya ,
1958
96.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR ,
1952
97.
98
W. Franke
Chem. Zentr. ,
1954
98.
99
V. V. Zolotarev
1938
99.
SHIOZAWA A., ICHIKAWA Y., KOMURO C., KURASHIGE S., MIYAZAKI H., YAMANAKA H., SAKAMOTO T.
Chemical and Pharmaceutical Bulletin ,
2011
100.
101
M. F. Shostakovskii
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk ,
1960
101.
102
F. Fichter
Helv. Chim. Acta ,
1922
102.
103
L. N. Bell
Dokl. Akad. Nauk SSSR ,
1956
103.
Rivalle C., Huel C., Bisagni E.
Journal of Heterocyclic Chemistry ,
1989
104.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR ,
1958
105.
106
F. Fichter
Helv. Chim. Acta ,
1927
106.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. ,
1961
107.
108
F. Fichter
Helv. Chim. Acta ,
1924
108.
Nemazany A., Haider N.
Journal of Heterocyclic Chemistry ,
1997
109.
110
M. F. Shostakovskii
Dokl. Akad. Nauk SSSR ,
1960
110.
111
M. Calvin
1956
111.
Clark R.D., Repke D.B., Kilpatrick A.T., Brown C.M., MacKinnon A.C., Clague R.U., Spedding M.
Journal of Medicinal Chemistry ,
1989
112.
Clark R.D., Repke D.B., Berger J., Nelson J.T., Kilpatrick A.T., Brown C.M., MacKinnon A.C., Clague R.U., Spedding M.
Journal of Medicinal Chemistry ,
1991
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.
Rohloff J.C., Dyson N.H., Gardner J.O., Alfredson T.V., Sparacino M.L., Robinson J.
Journal of Organic Chemistry ,
1993
121.
122
S. R. Rafikov
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk ,
1953
122.
Clark R.D., Michel A.D., Whiting R.L.
Progress in Medicinal Chemistry ,
1986
123.
Balczewski P., Mallon M.K., Street J.D., Joule J.A.
Journal of the Chemical Society Perkin Transactions 1 ,
1990
124.
125
K. A. Andrianov
Vysokomol. Soed. ,
1960
125.
126
J. Wiemannand Ch. Clachet
Compt. rend. ,
1948
126.
Nishiwaki N., Komatsu M., Ohshiro Y.
Synthesis ,
1991
127.
128
J. Wiemann
Bull. Soc. chim. France ,
1952
128.
J. Victory P., Teixid� J., I. Borrell J., Busquets N.
Heterocycles ,
1993
129.
Reed J.N., Rotchford J., Strickland D.
Tetrahedron Letters ,
1988
130.
Compagnon P., Gasquez F., Kimny T.
Bulletin des Sociétés Chimiques Belges ,
2010
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.
135
V. V. Korshak
Dokl. Akad. Nauk SSSR ,
1945
135.
136
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk ,
1954
136.
Mohareb R.M., Fahmy S.M.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences ,
1985
137.
Robinson J.M., Brent L.W., Chau C., Floyd K.A., Gillham S.L., McMahan T.L., Magda D.J., Motycka T.J., Pack M.J.
Journal of Organic Chemistry ,
1992
138.
139
I. L. Knunyants
1959
139.
Marcelis A.T., Van Der Plas H.C.
Tetrahedron ,
1989
140.
Gaidarova E.L., Borisenko A.A., Chumakov T.I., Mel'nikov A.V., Orlov I.S., Grishina G.V.
Tetrahedron Letters ,
1998
141.
142
1913
142.
143
Friedl.
143.
144
1912
144.
Friary R., Schwerdt J.H., Seidl V., Villani F.J.
Journal of Heterocyclic Chemistry ,
1990
145.
146
V. V. Korshak
Dokl. Akad. Nauk SSSR ,
1952
146.
Prasad K.R., Darbarwar M.
Synthetic Communications ,
1992
147.
Prasad K.R., Darbarwar M.
Organic Preparations and Procedures International ,
1995
148.
Fishwick C.W., Storr R.C., Manley P.W.
Journal of the Chemical Society Chemical Communications ,
1984
149.
150.
MIKI Y., TOMII O., UTSUNOMIYA M., TAKEMURA S., IKEDA M.
Chemical and Pharmaceutical Bulletin ,
2011
151.
Görlitzer K., Heinrici C.
Archiv der Pharmazie ,
1988
152.
153
1899
153.
154
Friedl.
154.
155
M. V. Mal'tsev
Izv. Vys. Ucheb. Zaved., Tsvet. Met. ,
1960
155.
Ojea V., Muinelo I., Figueroa M.C., Ruiz M., Quintela J.M.
Synlett ,
1995
156.
Světlík J., Tureček F., Hanuš V.
Journal of the Chemical Society Perkin Transactions 1 ,
1988
157.
SAMATOMO T., MIURA N., KONDO Y., YAMANAKA H.
Chemical and Pharmaceutical Bulletin ,
2011
158.
159
J. Tafel
Z. Elektrochem. ,
1911
159.
160
1912
160.
161
Friedl.
161.
162
1917
162.
163
Friedl.
163.
164
1917
164.
MISHIO S., HIROSE T., MINAMIDA A., MATSUMOTO J., MINAMI S.
Chemical and Pharmaceutical Bulletin ,
2011
165.
166
1917
166.
167
Friedl.
167.
168
1918
168.
169
Friedl.
169.
170
1918
170.
171
Friedl.
171.
Belicová A., Seman M., Milata V., Ilavský D., Ebringer L.
Folia Microbiologica ,
1997
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.
Natsugari H., Ikeura Y., Kiyota Y., Ishichi Y., Ishimaru T., Saga O., Shirafuji H., Tanaka T., Kamo I.
Journal of Medicinal Chemistry ,
1995
186.
Blanco M., Lorenzo M.G., Perillo I., Schapira C.B.
Journal of Heterocyclic Chemistry ,
1996
187.
188
Chem. Abs. ,
1955
188.
Couture A., Grandclaudon P., Simion C., Woisel P.
Journal of the Chemical Society Perkin Transactions 1 ,
1995
189.
Capuano L., Wamprecht C.
European Journal of Organic Chemistry ,
1986
190.
191
M. Matsui
Mem. Coll. Sci., Kyoto Univ. ,
1920
191.
192
E. Pannain
Rend. Classe Sci. fis. mat. nat. (5) ,
1908
192.
Linkert F., Laschat S., Knickmeier M.
European Journal of Organic Chemistry ,
1995
193.
194.
Paluszewski M., Sliwa W.
Australian Journal of Chemistry ,
1993
195.
196
E. Müller
Z. Elektrochem. ,
1910
196.
197
J. Sicher
Chem. Listy ,
1955
197.
Hirota T., Matsushita T., Sasaki K., Kashino S.
Heterocycles ,
1995
198.
Sasaki K., Rouf A.S., Hirota T.
Journal of Heterocyclic Chemistry ,
1996
199.
200
Ref. Zh. Khim. ,
1975
200.
201
A. Aladjem
1969
201.
Matusiak G.
Australian Journal of Chemistry ,
1999
202.
203
L. Andrieux
Compt. rend. ,
1929
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
206.
207
F. Fichter
"Organische Elektrochemie" ,
1942
207.
208
O. A. Reutov
"Teoreticheskie Problemy Organicheskoi Khimii" (Theoretical Problems in Organic Chemistry) ,
1956
208.
209
C. J. Haggerty
Trans. Am. Electrochem. Soc. ,
1929
209.
210
H. L. Wheeler
Chem. Zentr. ,
1908
210.
Rádl S., Hradil P.
Collection of Czechoslovak Chemical Communications ,
2009
211.
212
L. V. Pavlova
Zh. Obshch. Khim. ,
1965
212.
213
F. Yu. Rachinskii
"Khimiya Seraorganicheskikh Soedinenii, Soderzhashchikh-sya v Neftyakh i Nefteproduktakh" (Chemistry of Organo-sulphur Compounds Present in Petroleum and Petroleum Products) ,
1966
213.
214
L. V. Pavlova
1965
214.
215
N. D. Tomashov
Zh. Prikl. Khim. ,
1970
215.
216
A. P. Tomilov
Zhur. Prikl. Khim. ,
1959
216.
217
1925
217.
218
Chem. Zentr. II ,
1925
218.
219
G. I. Pustoshkin
Collected Papers "Biologicheskie Aktivnie Soedinenii" (Biologically Active Compounds) ,
1955
219.
220
K. Ziegler
Angew. Chem. ,
1955
220.
221
1960
221.
222
Chem. Abs. ,
1961
222.
223
1959
223.
Ikeura Y., Doi T., Fujishima A., Natsugari H.
Chemical Communications ,
1998
224.
Rajamanickam P., Shanmugam P.
Synthesis ,
1985
225.
Ibrahim N.S., Sadek K.U., Aziz S.I., Elnagdi M.H.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences ,
1985
226.
Nozulak J., Kalkman H.O., Floerscheim P., Hoyer D., Schoeffter P., Buerki H.R.
Journal of Medicinal Chemistry ,
1995
228.
229
1959
229.
230
Chem. Abs. ,
1962
230.
231
1960
231.
232
Chem. Abs. ,
1960
232.
233.
Ritter J., Gleiter R.
European Journal of Organic Chemistry ,
1997
234.
235
R. Peffen
1967
235.
236
P. Peshev
Rev. internat. hautes Temperat. et Réfract. ,
1969
236.
237
P. Peshev
Rev. internat. hautes Temperat. et Réfract. ,
1969
237.
238
Brown G P
Am. Chem. Soc., Polymer Preprints ,
1964
238.
El-Reedy A.M., Ibrahim M.K., Hussain S.M., Moharram H.H.
Journal für praktische Chemie ,
1989
239.
240
W. A. Waters
"The Chemistry of Free Radicals" ,
1948
240.
241
M. S. Kharasch
"Grignard Reactions of Nonmetallic Substances" ,
1954
241.
242
N. N. Seroenov
"O Nekotorykh Problemakh Khimicheskoi Kinetiki i Reaktsionnoi Sposobnosti" (Some Problems in Chemical Kinetics and Reactivity) ,
1958
242.
Roussel C., Mercier A., Cartier M.
Journal of Organic Chemistry ,
1987
243.
244
C. Wilson
Record. Chem. Prog. ,
1949
244.
245
G. A. Meerson
1958
245.
Ridley A., Taylor W.
Australian Journal of Chemistry ,
1987
246.
247
E. I. Levkoeva
Khim. Geterotsikl. Soed. ,
1976
247.
248
M. Ya. Fioshin
Plasticheskie Massy ,
1960
248.
249
A. I. Fedorova
Dokl. Akad. Nauk SSSR ,
1961
249.
250
D. Goerrig
1955
250.
Görlitzer K., Bartke U., Schmidt E.
Archiv der Pharmazie ,
1991
251.
252
D. Goerrig
1956
252.
Mohareb R.M., Zohdi H.F., Sherif S.M., Wardkhan W.W.
Tetrahedron ,
1994
253.
Bracher F.
Journal of Heterocyclic Chemistry ,
1993
254.
Nutaitis C.F., Marsh S.R.
Journal of Heterocyclic Chemistry ,
1992
255.
Reimann E., Benend H.
Archiv der Pharmazie ,
1994
256.
Winters G., Sala A., De Paoli A., Ferri V.
Synthesis ,
1984
257.
258
P. P. Alexander
Metals Alloys ,
1938
258.
259
V. Elyutin
Trudy Moskov. Inst. Stali ,
1939
259.
Cochennec C., Rocca P., Marsais F., Godard A., Quéguiner G.
Journal of the Chemical Society Perkin Transactions 1 ,
1995
260.
261
C. Friedel
Ann. Chim. Phys. ,
1876
261.
Gramain J., Troin Y., Vallée-Goyet D.
Tetrahedron ,
1991
262.
Jahangir, Brook M.A., MacLean D.B., Holland H.L.
Canadian Journal of Chemistry ,
1987
263.
264.
Reimann E., Renz H.
Monatshefte fur Chemie ,
1994
265.
Jahangir, Brook M.A., Maclean D.B., Holland H.L.
Tetrahedron ,
1987
266.
267.
B. Repke D., D. Clark R., T. Nelson J.
Heterocycles ,
1988
268.
A. Szarek W., W. Rey A., B. MacLean D.
Heterocycles ,
1991
269.
He H.Y., Faulkner D.J.
Journal of Organic Chemistry ,
1991
270.
Ciufolini M.A., Byrne N.E.
Journal of the American Chemical Society ,
1991
271.
Gunawardana G.P., Koehn F.E., Lee A.Y., Clardy J., He H.Y., Faulkner D.J.
Journal of Organic Chemistry ,
1992
272.
McCarthy P.J., Pitts T.P., Gunawardana G.P., Kelly-Borges M., Pomponi S.A.
Journal of Natural Products ,
1992
273.
274
J. Johnston
Edin. J. Sci. (New Ser.) ,
1831
274.
275
H. Moissan
Compt. rend. ,
1895
275.
276
St. C. H. Deville
Ann. Chim. Phys. ,
1859
276.
277
St. C. H. Deville
Ann. Chim. Phys. ,
1859
277.
Carte B.K., DeBrosse C., Eggleston D., Hemling M., Mentzer M., Poehland B., Troupe N., Westley J.W., Hecht S.M.
Tetrahedron ,
1990
278.
279
B. de Jassonneix
Compt. rend. ,
1906
279.
280
B. de Jassonneix
Compt. rend. ,
1906
280.
281
B. de Jassonneix
Compt. rend. ,
1906
281.
282
B. de Jassonneix
Compt. rend. ,
1906
282.
283
H. Moissan
Compt. rend. ,
1902