-
1
-
-
80955145694
-
-
For the biological activities of some indolylpyrazole derivatives, see: (a)
-
For the biological activities of some indolylpyrazole derivatives, see: (a) Zhang, D.; Wang, G.; Zhao, G.; Xu, W.; Huo, L. Eur. J. Med. Chem. 2011, 46, 5868-5877.
-
(2011)
Eur. J. Med. Chem.
, vol.46
, pp. 5868-5877
-
-
Zhang, D.1
Wang, G.2
Zhao, G.3
Xu, W.4
Huo, L.5
-
2
-
-
79957743791
-
-
Pierce, L. T.; Cahill, M. M.; McCarthy, F. O. Tetrahedron 2011, 67, 4601-4611.
-
(2011)
Tetrahedron
, vol.67
, pp. 4601-4611
-
-
Pierce, L.T.1
Cahill, M.M.2
McCarthy, F.O.3
-
3
-
-
77953129279
-
-
Diana, P.; Carbone, A.; Barraja, P.; Kelter, G.; Fiebig, H.-H.; Cirrincione, G. Bioorg. Med. Chem. 2010, 18, 4524-4529.
-
(2010)
Diana, P.; Carbone, A.; Barraja, P.; Kelter, G.; Fiebig, H.-H.; Cirrincione, G. Bioorg. Med. Chem.
, vol.18
, pp. 4524-4529
-
-
-
4
-
-
77954213226
-
-
Zhang, N.; Ayral-Kaloustian, S.; Anderson, J. T.; Nguyen, T.; Das, S.; Venkatesan, A. M.; Brooijmans, N.; Lucas, J.; Yu, K.; Hollander, I.; Mallon, R. Bioorg. Med. Chem. Lett. 2010, 20, 3526-3529.
-
(2010)
Bioorg. Med. Chem. Lett.
, vol.20
, pp. 3526-3529
-
-
Zhang, N.1
Ayral-Kaloustian, S.2
Anderson, J.T.3
Nguyen, T.4
Das, S.5
Venkatesan, A.M.6
Brooijmans, N.7
Lucas, J.8
Yu, K.9
Hollander, I.10
Mallon, R.11
-
5
-
-
77953134237
-
-
Velankar, A. D.; Quintini, G.; Prabhu, A.; Weber, A.; Hunaeus, G.; Voland, B.; Wuest, M.; Orjeda, C.; Harel, D.; Varghese, S.; Gore, V.; Patil, M.; Gayke, D.; Herdemann, M.; Heit, I.; Zaliani, A. Bioorg. Med. Chem. 2010, 18, 4547-4559.
-
(2010)
Bioorg. Med. Chem.
, vol.18
, pp. 4547-4559
-
-
Velankar, A.D.1
Quintini, G.2
Prabhu, A.3
Weber, A.4
Hunaeus, G.5
Voland, B.6
Wuest, M.7
Orjeda, C.8
Harel, D.9
Varghese, S.10
Gore, V.11
Patil, M.12
Gayke, D.13
Herdemann, M.14
Heit, I.15
Zaliani, A.16
-
6
-
-
35148824608
-
-
Diana, P.; Carbone, A.; Barraja, P.; Martorana, A.; Gia, O.; DallaVia, L.; Cirrincione, G. Bioorg. Med. Chem. Lett. 2007, 17, 6134-6137.
-
(2007)
Bioorg. Med. Chem. Lett.
, vol.17
, pp. 6134-6137
-
-
Diana, P.1
Carbone, A.2
Barraja, P.3
Martorana, A.4
Gia, O.5
DallaVia, L.6
Cirrincione, G.7
-
7
-
-
33750893617
-
-
Sivaprasad, G.; Perumal, P. T.; Prabavathy, V. R.; Mathivanan, N. Bioorg. Med. Chem. Lett. 2006, 16, 6302-6305.
-
(2006)
Bioorg. Med. Chem. Lett.
, vol.16
, pp. 6302-6305
-
-
Sivaprasad, G.1
Perumal, P.T.2
Prabavathy, V.R.3
Mathivanan, N.4
-
8
-
-
41649085357
-
-
Reddy, M. V. R.; Billa, V. K.; Pallela, V. R.; Mallireddigari, M. R.; Boominathan, R.; Gabriel, J. L.; Reddy, E. P. Bioorg. Med. Chem. 2008, 16, 3907-3916.
-
(2008)
Bioorg. Med. Chem.
, vol.16
, pp. 3907-3916
-
-
Reddy, R.M.V.1
Billa, V.2
Pallela, V.3
Mallireddigari, M.4
Boominathan, R.5
Gabriel, J.6
Reddy, E.7
-
9
-
-
79953196824
-
-
For the synthesis of indolylpyrazole derivatives by a transition metal-catalyzed coupling reactions see.
-
For the synthesis of indolylpyrazole derivatives by a transition metal-catalyzed coupling reactions, see: (a) Khan, T. A.; Kumar, S.; Venkatesh, C.; Ila, H. Tetrahedron 2011, 67, 2961-2968.
-
(2011)
Tetrahedron
, vol.67
, pp. 2961-2968
-
-
Khan, T.A.1
Kumar, S.2
Venkatesh, C.3
Ila, H.4
-
10
-
-
77955156824
-
-
Delaunay, T.; Genix, P.; Es-Sayed, M.; Vors, J.-P.; Monteiro, N.; Balme, G. Org. Lett. 2010, 12, 3328-3331.
-
(2010)
Org. Lett.
, vol.12
, pp. 3328-3331
-
-
Delaunay, T.1
Genix, P.2
Es-Sayed, M.3
Vors, J.-P.4
Monteiro, N.5
Balme, G.6
-
11
-
-
79960316996
-
-
Delaunay, T.; Es-Sayed, M.; Vors, J.-P.; Monteiro, N.; Balme, G. Eur. J. Org. Chem. 2011, 3837-3848.
-
(2011)
Eur. J. Org. Chem.
, pp. 3837-3848
-
-
Delaunay, T.1
Es-Sayed, M.2
Vors, J.-P.3
Monteiro, N.4
Balme, G.5
-
12
-
-
84864595859
-
-
Bobko, M. A.; Kaura, A. C.; Evans, K. A.; Su, D.-S. Org. Lett. 2012, 14, 3906-3908.
-
(2012)
Org. Lett.
, vol.14
, pp. 3906-3908
-
-
Bobko, M.A.1
Kaura, A.C.2
Evans, K.A.3
Su, D.-S.4
-
13
-
-
34547946209
-
-
Stansfield, I.; Pompei, M.; Conte, I.; Ercolani, C.; Migliaccio, G.; Jairaj, M.; Giuliano, C.; Rowley, M.; Narjes, F. Bioorg. Med. Chem. Lett. 2007, 17, 5143-5149.
-
(2007)
Bioorg. Med. Chem. Lett.
, vol.17
, pp. 5143-5149
-
-
Stansfield, I.1
Pompei, M.2
Conte, I.3
Ercolani, C.4
Migliaccio, G.5
Jairaj, M.6
Giuliano, C.7
Rowley, M.8
Narjes, F.9
-
16
-
-
84859608186
-
-
For The Synthesis Of Indolylpyrazole Derivatives Via A Sequential Construction Of Pyrazole And Indole Rings See:
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For the synthesis of indolylpyrazole derivatives via a sequential construction of pyrazole and indole rings, see: (a) Usachev, B. I.; Obydennov, D. L.; Roschenthaler, G.-V.; Sosnovskikh, V. Y. J. Fluorine Chem. 2012, 137, 22-26.
-
(2012)
J. Fluorine Chem.
, vol.137
, pp. 22-26
-
-
Usachev, B.I.1
Obydennov, D.L.2
Roschenthaler, G.-V.3
Sosnovskikh, V.Y.4
-
17
-
-
84857355341
-
-
Usachev, B. I.; Obydennov, D. L.; Sosnovskikh, V. Y. J. Fluorine Chem. 2012, 135, 278-284.
-
(2012)
J. Fluorine Chem.
, vol.135
, pp. 278-284
-
-
Usachev, B.I.1
Obydennov, D.L.2
Sosnovskikh, V.3
-
18
-
-
66949178750
-
-
(c) Usachev, B. I.; Obydennov, D. L.; Kodess, M. I.; Sosnovskikh, V. Y. Tetrahedron Lett. 2009, 50, 4446-4448.
-
(2009)
Tetrahedron Lett.
, vol.50
, pp. 4446-4448
-
-
Usachev, B.I.1
Obydennov, D.L.2
Kodess, M.I.3
Sosnovskikh, V.Y.4
-
19
-
-
77955725805
-
-
Usachev, B. I.; Obydennov, D. L.; Kodess, M. I.; Roschenthaler, G.-V.; Sosnovskikh, V. Y. Russ. Chem. Bull. Int. Ed. 2009, 58, 1248-1252.
-
(2009)
Usachev, B. I.; Obydennov, D. L.; Kodess, M. I.; Roschenthaler, G.-V.; Sosnovskikh, V. Y. Russ. Chem. Bull. Int. Ed.
, vol.58
, pp. 1248-1252
-
-
-
20
-
-
84865480168
-
-
Sechi, M.; Innocenti, A.; Pala, N.; Rogolino, D.; Carcelli, M.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2012, 22, 5801-5806.
-
(2012)
Bioorg. Med. Chem. Lett.
, vol.22
, pp. 5801-5806
-
-
Sechi, M.1
Innocenti, A.2
Pala, N.3
Rogolino, D.4
Carcelli, M.5
Scozzafava, A.6
Supuran, C.7
-
21
-
-
84889027225
-
-
A One-pot Synthesis Of Indolylpyrazole From 15-di(p-tolyl)pentane 1, 35-trione and phenylhydrazine hydrochloride was also reported however the paper prepared only one compound in very low yield ( 25%) in refluxing EtOH, see:
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A one-pot synthesis of indolylpyrazole from 1,5-di(p-tolyl)pentane-1,3,5- trione and phenylhydrazine hydrochloride was also reported; however, the paper prepared only one compound in very low yield (25%) in refluxing EtOH, see:
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-
-
-
22
-
-
0011168762
-
-
Jukic, M.; Cetina, M.; Pavlovic, G.; Rapic, V. Struct. Chem. 1999, 10, 85-90.
-
(1999)
Struct. Chem.
, vol.10
, pp. 85-90
-
-
Jukic, M.1
Cetina, M.2
Pavlovic, G.3
Rapic, V.4
-
23
-
-
84864979992
-
-
Kim, S. H.; Lee, S.; Kim, S. H.; Lim, J. W.; Kim, J. N. Tetrahedron Lett. 2012, 53, 4979-4983.
-
(2012)
Tetrahedron Lett.
, vol.53
, pp. 4979-4983
-
-
Kim, S.H.1
Lee, S.2
Kim, S.H.3
Lim, J.W.4
Kim, J.5
-
24
-
-
0032236944
-
-
Dandia, A.; Rani, B.; Saha, M. Indian J. Chem. Technol. 1998, 5, 159-162.
-
(1998)
Indian J. Chem. Technol.
, vol.5
, pp. 159-162
-
-
Dandia, A.1
Rani, B.2
Saha, M.3
-
25
-
-
84889076323
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The Formation Of Pyrazole Ring Might Occur Preferentially Over The Indole Ring.1f3c3d Thus 3a 3a' And The Corresponding Hydrazones Of 3a And 3a' Could Be The Possible Intermediates. In this respect, the reaction of 1a with a limited amount (0.9 equiv) of phenylhydrazine hydrochloride was examined at low temperature (EtOH, 40 oC) in order to separate major intermediate(s) such as 3a or the hydrazone of 3a; however, so many spots were observed including 4a and 5a, and we failed to identify the major intermediate(s). Thus, we cannot exclude the possibility for the initial formation of an indole ring and a subsequent pyrazole formation at this stage
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The formation of pyrazole ring might occur preferentially over the indole ring.1f,3c,3d Thus, 3a, 3a', and the corresponding hydrazones of 3a and 3a' could be the possible intermediates. In this respect, the reaction of 1a with a limited amount (0.9 equiv) of phenylhydrazine hydrochloride was examined at low temperature (EtOH, 40 oC) in order to separate major intermediate(s) such as 3a or the hydrazone of 3a; however, so many spots were observed including 4a and 5a, and we failed to identify the major intermediate(s). Thus, we cannot exclude the possibility for the initial formation of an indole ring and a subsequent pyrazole formation at this stage.
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-
-
-
26
-
-
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-
-
Qu, J.; Kumar, N.; Alamgir, M.; Black, D. StC. Tetrahedron Lett. 2009, 50, 5628-5630.
-
(2009)
StC. Tetrahedron Lett.
, vol.50
, pp. 5628-5630
-
-
Qu, J.1
Kumar, N.2
Alamgir, M.3
Black, D.4
-
27
-
-
84970571276
-
-
(a) Black, D. StC.; Deb-Das, R. B.; Kumar, N. Aust. J. Chem. 1992, 45, 611-621.
-
(1992)
Aust. J. Chem.
, vol.45
, pp. 611-621
-
-
Black D., StC.1
Deb-Das, R.B.2
Kumar, N.3
-
28
-
-
80052559886
-
-
Butin, A. V.; Uchuskin, M. G.; Pilipenko, A. S.; Serdyuk, O. V.; Trushkov, I. V. Tetrahedron Lett. 2011, 52, 5255-5258.
-
(2011)
Tetrahedron Lett.
, vol.52
, pp. 5255-5258
-
-
Butin, A.V.1
Uchuskin, M.G.2
Pilipenko, A.S.3
Serdyuk, O.V.4
Trushkov, I.5
-
29
-
-
84963455558
-
-
Dandia, A.; Sehgal, V.; Upreti, M. Phosphorous, Sulfur and Silicon 1995, 105, 93-99.
-
(1995)
Phosphorous Sulfur and Silicon
, vol.105
, pp. 93-99
-
-
Dandia, A.1
Sehgal, V.2
Upreti, M.3
-
30
-
-
84889035571
-
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During the evaluation process one of the reviewers suggested the synthesis of indolylpyrazoles with other 1 ,3,5-triketones. Thus, we prepared 1,5-di(2-pyridyl)-1,3,5-pentanetrione (1c) according to the reported method and examined the reaction with
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During the evaluation process one of the reviewers suggested the synthesis of indolylpyrazoles with other 1,3,5-triketones. Thus, we prepared 1,5-di(2-pyridyl)-1,3,5-pentanetrione (1c) according to the reported method and examined the reaction with
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31
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84856750858
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-
For the preparation of 1c
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For the preparation of 1c: Saadeh, H. A.; Abu Shairah, E. A.; Charef, N.; Mubarak, M. S. J. Appl. Polym. Sci. 2012, 124, 2717-2724.
-
(2012)
J. Appl. Polym. Sci.
, vol.124
, pp. 2717-2724
-
-
Saadeh, H.1
Shairah, A.E.2
Charef, N.3
Mubarak, M.4
-
33
-
-
58149147155
-
-
Chou, S.-Y.; Chen, C.-J.; Tsai, S.-L.; Sheu, H.-S.; Lee, G.-H.; Lai, C. K. Tetrahedron 2009, 65, 1130-1139.
-
(2009)
Tetrahedron
, vol.65
, pp. 1130-1139
-
-
Chou, S.-Y.1
Chen, C.-J.2
Tsai, S.-L.3
Sheu, H.-S.4
Lee, G.-H.5
Lai, C.6
-
34
-
-
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-
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For the synthesis and biological activity of pyrimidylindole derivatives, see: (a)
-
For the synthesis and biological activity of pyrimidylindole derivatives, see: (a) Walker, S. R.; Carter, E. J.; Huff, B. C.; Morris, J. C. Chem. Rev. 2009, 109, 3080-3098.
-
(2009)
Chem. Rev.
, vol.109
, pp. 3080-3098
-
-
Walker, S.1
Carter, E.2
Huff, B.3
Morris, J.C.4
-
35
-
-
66449124044
-
-
Akue-Gedu, R.; Debiton, E.; Ferandin, Y.; Meijer, L.; Prudhomme, M.; Anizon, F.; Moreau, P. Bioorg. Med. Chem. 2009, 17, 4420-4424.
-
(2009)
Bioorg. Med. Chem.
, vol.17
, pp. 4420-4424
-
-
Akue-Gedu, R.1
Debiton, E.2
Ferandin, Y.3
Meijer, L.4
Prudhomme, M.5
Anizon, F.6
Moreau, P.7
-
37
-
-
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-
-
The formation of appreciable amounts of acetophenone and 2-amino-4-hydroxy-6-phenylpyrimidine was observed on TLC. 13. Actually, the compound 13 existed as a keto/enol (2:3) tautomeric mixture in its 1H NMR spectrum. For the similar keto/enol equilibration of 1-substituted-2-azinyl-1- ethanones, see
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The formation of appreciable amounts of acetophenone and 2-amino-4-hydroxy-6-phenylpyrimidine was observed on TLC. 13. Actually, the compound 13 existed as a keto/enol (2:3) tautomeric mixture in its 1H NMR spectrum. For the similar keto/enol equilibration of 1-substituted-2-azinyl-1- ethanones, see: (a) Katritzky, A. R.; Abdel-Fattah, A. A. A.; Akhmedova, R. G. ARKIVOC 2005 (vi) 329-338.
-
(2005)
ARKIVOC
, vol.6
, pp. 329-338
-
-
Katritzky, A.1
Abdel-Fattah, A.A.A.2
Akhmedova, R.3
-
38
-
-
34347251257
-
-
Prekupec, S.; Makuc, D.; Plavec, J.; Suman, L.; Kralj, M.; Pavelic, K.; Balzarini, J.; De Clerq, E.; Mintas, M.; Raic-Malic, S. J. Med. Chem. 2007, 50, 3037-3045.
-
(2007)
J. Med. Chem.
, vol.50
, pp. 3037-3045
-
-
Prekupec, S.1
Makuc, D.2
Plavec, J.3
Suman, L.4
Kralj, M.5
Pavelic, K.6
Balzarini, J.7
De Clerq, E.8
Mintas, M.9
Raic-Malic, S.10
-
39
-
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The regioisomeric indolylpyrazole 5a was not formed at all in the reaction, and the result could be a strong evidence for the suggested mechanism
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The regioisomeric indolylpyrazole 5a was not formed at all in the reaction, and the result could be a strong evidence for the suggested mechanism.
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