SCOPUS 정보 검색 플랫폼

Volumn 10, Issue 25, 2012, Pages 4916-4925

Study of N1-alkylation of indoles from the reaction of 2(or 3)-aminoindole-3-(or 2)carbonitriles with DMF-dialkylacetals

(7) Loidreau, Yvonnick a,b Melissen, Sigismund b Levacher, Vincent b,c Logé, Cédric d Graton, Jérôme d Le Questel, Jean Yves d Besson, Thierry a,b

a UNIVERSITÉ DE ROUEN (France)

b IRCOF (France)

c UNIVERSITÉ ET INSA DE ROUEN (France)

d UNIVERSITÉ DE NANTES (France)

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVITY;

BUILDING BLOCKES; CARBONITRILES; DESCRIPTORS; DFT CALCULATION; ELECTROSTATIC POTENTIALS;

ISOMERS;

ACETAL DERIVATIVE; INDOLE DERIVATIVE; N,N DIMETHYLFORMAMIDE; NITRILE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STATIC ELECTRICITY;

ACETALS; ALKYLATION; DIMETHYLFORMAMIDE; INDOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITRILES; STATIC ELECTRICITY;

EID: 84862174385 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c2ob25747e Document Type: Article

Times cited : (13)

References (56)

1
- 0001477089
- R. F. Abdulla R. S. Brinkmeyer Tetrahedron 1979 35 1675
- (1979) Tetrahedron , vol.35 , pp. 1675
- Abdulla, R.F.¹ Brinkmeyer, R.S.²

2
- 45949119337
- J. T. Gupton J. F. Miller R. D. Bryant P. R. Maloney B. S. Foster Tetrahedron 1987 43 1747
- (1987) Tetrahedron , vol.43 , pp. 1747
- Gupton, J.T.¹ Miller, J.F.² Bryant, R.D.³ Maloney, P.R.⁴ Foster, B.S.⁵

3
- 0031592601
- P. L. Anelli M. Brocchetta D. Palano M. Visigalli Tetrahedron Lett. 1997 38 2367
- (1997) Tetrahedron Lett. , vol.38 , pp. 2367
- Anelli, P.L.¹ Brocchetta, M.² Palano, D.³ Visigalli, M.⁴

4
- 79955480567
- P. Belov V. L. Campanella A. W. Smith R. Priefer Tetrahedron Lett. 2011 52 2776
- (2011) Tetrahedron Lett. , vol.52 , pp. 2776
- Belov, P.¹ Campanella, V.L.² Smith, A.W.³ Priefer, R.⁴

5
- 77955413543
- K. F. Biegasiewicz J. D. St. Denis V. M. Carroll R. Priefer Tetrahedron Lett. 2010 51 4408
- (2010) Tetrahedron Lett. , vol.51 , pp. 4408
- Biegasiewicz, K.F.¹ St. Denis, J.D.² Carroll, V.M.³ Priefer, R.⁴

6
- 38549127336
- Yu. B. Sinkevich A. E. Shchekotikhin Yu. N. Luzinov V. N. Buyanov L. V. Kovalenko Chem. Heterocycl. Compd. 2007 43 1252
- (2007) Chem. Heterocycl. Compd. , vol.43 , pp. 1252
- Sinkevich, Yu.B.¹ Shchekotikhin, A.E.² Luzinov, Yu.N.³ Buyanov, V.N.⁴ Kovalenko, L.V.⁵

7
- 0009556787
- A. Holy Tetrahedron Lett. 1972 13 585
- (1972) Tetrahedron Lett. , vol.13 , pp. 585
- Holy, A.¹

8
- 0021198474
- R. W. Middleton H. Monney J. Parrick Synthesis 1984 740
- (1984) Synthesis , pp. 740
- Middleton, R.W.¹ Monney, H.² Parrick, J.³

9
- 0016736969
- For various examples of this strategy for the synthesis of bioactive molecules see
- K. D. Phillips J. P. Horwitz J. Org. Chem. 1975 40 1856
- (1975) J. Org. Chem. , vol.40 , pp. 1856
- Phillips, K.D.¹ Horwitz, J.P.²

10
- 84859175803
- M. A. Vodolazhenko N. Yu. Gorobets S. A. Yermolayev V. V. Musatov V. A. Chebanov S. M. Desenko RSC Adv. 2012 2 1106
- (2012) RSC Adv. , vol.2 , pp. 1106
- Vodolazhenko, M.A.¹ Gorobets, N.Yu.² Yermolayev, S.A.³ Musatov, V.V.⁴ Chebanov, V.A.⁵ Desenko, S.M.⁶

11
- 77955422785
- J. D. St Denis J. S. Gordon IV V. M. Carroll R. Priefer Synthesis 2010 1590
- (2010) Synthesis , pp. 1590
- St Denis, J.D.¹ Gordon, I.V.J.S.² Carroll, V.M.³ Priefer, R.⁴

12
- 34548247722
- E. Rossignol A. Youssev P. Moreau M. Prudhomme F. Anizon Tetrahedron 2007 63 10169
- (2007) Tetrahedron , vol.63 , pp. 10169
- Rossignol, E.¹ Youssev, A.² Moreau, P.³ Prudhomme, M.⁴ Anizon, F.⁵

13
- 36749074458
- G. Simon H. Couthon-Gourves J.-P. Haelters B. Corbel N. Keravec F. Michaud L. Meijer J. Heterocycl. Chem. 2007 44 793
- (2007) J. Heterocycl. Chem. , vol.44 , pp. 793
- Simon, G.¹ Couthon-Gourves, H.² Haelters, J.-P.³ Corbel, B.⁴ Keravec, N.⁵ Michaud, F.⁶ Meijer, L.⁷

14
- 24944478098
- M. del C. Cruz J. Tamariz Tetrahedron 2005 61 10061
- (2005) Tetrahedron , vol.61 , pp. 10061
- Cruz, M.D.C.¹ Tamariz, J.²

15
- 4344680844
- For various examples of this strategy for the synthesis of bioactive molecules see
- N. Y. Gorobets B. H. Yousefi F. Belaj C. O. Kappe Tetrahedron 2004 60 8633
- (2004) Tetrahedron , vol.60 , pp. 8633
- Gorobets, N.Y.¹ Yousefi, B.H.² Belaj, F.³ Kappe, C.O.⁴

16
- 77953121625
- A. Foucourt C. Dubouilh-Benard E. Chosson C. Corbière C. Buquet M. Iannelli B. Leblond F. Marsais T. Besson Tetrahedron 2010 66 4495
- (2010) Tetrahedron , vol.66 , pp. 4495
- Foucourt, A.¹ Dubouilh-Benard, C.² Chosson, E.³ Corbière, C.⁴ Buquet, C.⁵ Iannelli, M.⁶ Leblond, B.⁷ Marsais, F.⁸ Besson, T.⁹

17
- 69049097421
- Z. Rachid M. MacPhee C. Williams M. Torodova B. J. Jean-Claude Bioorg. Med. Chem. Lett. 2009 19 5505
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 5505
- Rachid, Z.¹ MacPhee, M.² Williams, C.³ Torodova, M.⁴ Jean-Claude, B.J.⁵

18
- 33745123646
- J. Domarkas F. Dudouit C. Williams Q. Qiyu R. Banerjee F. Brahimi B. J. Jean-Claude J. Med. Chem. 2006 49 3544
- (2006) J. Med. Chem. , vol.49 , pp. 3544
- Domarkas, J.¹ Dudouit, F.² Williams, C.³ Qiyu, Q.⁴ Banerjee, R.⁵ Brahimi, F.⁶ Jean-Claude, B.J.⁷

19
- 11444265468
- D. S. Yoon H. Han T. M. Stark J. C. Haber B. T. Gregg S. B. Stankovich Org. Lett. 2004 6 4775
- (2004) Org. Lett. , vol.6 , pp. 4775
- Yoon, D.S.¹ Han, H.² Stark, T.M.³ Haber, J.C.⁴ Gregg, B.T.⁵ Stankovich, S.B.⁶

20
- 0035899182
- For a review on the role of DMF-DMA as a building block in heterocyclic chemistry see
- H. R. Tsou N. Mamuya B. D. Johnson M. F. Reich B. C. Gruber F. Ye R. Nilakantan R. Shen C. Discafani R. DeBlanc R. Davis F. E. Koehn L. M. Greenberger Y. F. Wang A. Wissner J. Med. Chem. 2001 44 2719
- (2001) J. Med. Chem. , vol.44 , pp. 2719
- Tsou, H.R.¹ Mamuya, N.² Johnson, B.D.³ Reich, M.F.⁴ Gruber, B.C.⁵ Ye, F.⁶ Nilakantan, R.⁷ Shen, R.⁸ Discafani, C.⁹ Deblanc, R.¹⁰ Davis, R.¹¹ Koehn, F.E.¹² Greenberger, L.M.¹³ Wang, Y.F.¹⁴ Wissner, A.¹⁵

21
- 70349245461
- For a paper on the thermal effect of microwaves see
- F. A. Abu-Shanab S. M. S. Sherif A. S. Mousa J. Heterocycl. Chem. 2009 46 801
- (2009) J. Heterocycl. Chem. , vol.46 , pp. 801
- Abu-Shanab, F.A.¹ Sherif, S.M.S.² Mousa, A.S.³

22
- 70350031640
- D. Obermayer B. Guttmann C. O. Kappe Angew. Chem., Int. Ed. 2009 48 8321
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 8321
- Obermayer, D.¹ Guttmann, B.² Kappe, C.O.³

23
- 80052046345
- For a complete review see
- A. Nathubhai R. Patterson T. J. Woodman H. E. C. Sharp M. T. Y. Chui H. H. K. Chung S. W. S. Lau J. Zheng M. D. Lloyd A. S. Thompson M. D. Threadgill Org. Biomol. Chem. 2011 9 6089
- (2011) Org. Biomol. Chem. , vol.9 , pp. 6089
- Nathubhai, A.¹ Patterson, R.² Woodman, T.J.³ Sharp, H.E.C.⁴ Chui, M.T.Y.⁵ Chung, H.H.K.⁶ Lau, S.W.S.⁷ Zheng, J.⁸ Lloyd, M.D.⁹ Thompson, A.S.¹⁰ Threadgill, M.D.¹¹

24
- 84986259048
- in, ed. O. A. Attanasi and D. Spinelli, Italian Society of Chemistry, Roma, p. 315 Synthesis of 2-aminoindole-3-carbonitrile (2) was realized in two steps from 2-bromoaniline via an intermediate N-(2-bromophenyl)-2,2,2- trifluoroacetamide following the route described in
- C. S. Harris, L. Hennequin, R. Morgentin and G. Pasquet, in Targets in Heterocyclic Systems - Chemistry and Properties, ed., O. A. Attanasi, and, D. Spinelli, Italian Society of Chemistry, Roma, 2010, vol. 14, p. 315
- (2010) Targets in Heterocyclic Systems - Chemistry and Properties , vol.14
- Harris, C.S.¹ Hennequin, L.² Morgentin, R.³ Pasquet, G.⁴

25
- 77951169071
- The 6-nitro analogue (3) was obtained in good yield by heating a mixture of 2-fluoro-5-nitroaniline and malononitrile in dimethylformamide in the presence of potassium carbonate, as described in
- X. Yang H. Fu R. Qiao Y. Jiang Y. Zhao Adv. Synth. Catal. 2010 352 1033
- (2010) Adv. Synth. Catal. , vol.352 , pp. 1033
- Yang, X.¹ Fu, H.² Qiao, R.³ Jiang, Y.⁴ Zhao, Y.⁵

26
- 0035467638
- 3-Aminoindole-2-carbonitriles (8 and 9) were synthesized as published in recent papers by Koutentis and his group from the corresponding anthranilonitriles in two steps via intermediates 2-(4-chloro-5H-1,2,3- dithiazol-5-ylideneamino)benzonitriles obtained after reaction of the starting material with 4,5-dichloro-1,2,3-dithiazolium chloride (Appel's salt) in dichloromethane at room temperature
- Yu. M. Volovenko T. A. Volovnenko Chem. Heterocycl. Compd. 2001 37 1092
- (2001) Chem. Heterocycl. Compd. , vol.37 , pp. 1092
- Volovenko, Yu.M.¹ Volovnenko, T.A.²

27
- 69249173341
- S. S. Michaelidou P. A. Koutentis Tetrahedron 2009 65 8428
- (2009) Tetrahedron , vol.65 , pp. 8428
- Michaelidou, S.S.¹ Koutentis, P.A.²

28
- 71649096942
- S. S. Michaelidou P. A. Koutentis Tetrahedron 2010 66 685
- (2010) Tetrahedron , vol.66 , pp. 685
- Michaelidou, S.S.¹ Koutentis, P.A.²

29
- 77955413259
- P. A. Koutentis S. S. Michaelidou Tetrahedron 2010 66 6032
- (2010) Tetrahedron , vol.66 , pp. 6032
- Koutentis, P.A.¹ Michaelidou, S.S.²

30
- 45949085044
- C. Logé A. Testard V. Thiéry O. Lozach M. Blairvacq J.-M. Robert L. Meijer T. Besson Eur. J. Med. Chem. 2008 43 1469
- (2008) Eur. J. Med. Chem. , vol.43 , pp. 1469
- Logé, C.¹ Testard, A.² Thiéry, V.³ Lozach, O.⁴ Blairvacq, M.⁵ Robert, J.-M.⁶ Meijer, L.⁷ Besson, T.⁸

31
- 33744927132
- A. Testard C. Logé B. Léger J.-M. Robert O. Lozach M. Blairvacq L. Meijer V. Thiéry T. Besson Bioorg. Med. Chem. Lett. 2006 16 3419
- (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 3419
- Testard, A.¹ Logé, C.² Léger, B.³ Robert, J.-M.⁴ Lozach, O.⁵ Blairvacq, M.⁶ Meijer, L.⁷ Thiéry, V.⁸ Besson, T.⁹

32
- 0038066125
- Lost dissipation factor (tan δ) expresses the capacity of a molecule or a material to transform electromagnetic energy into thermal energy. A high susceptibility to microwaves is characterized by a high value (>0.5) of tan δ. For more details see
- F. R. Alexandre A. Berecibar R. Wrigglesworth T. Besson Tetrahedron Lett. 2003 44 4455
- (2003) Tetrahedron Lett. , vol.44 , pp. 4455
- Alexandre, F.R.¹ Berecibar, A.² Wrigglesworth, R.³ Besson, T.⁴

33
- 0032330265
- For recent examples of reactants (e.g. formamides, dimethylsulfoxide) that can be the source of key reactants (carbon monoxide, amines, formyl group and formate) in microwave-assisted organic synthesis see
- C. Gabriel S. Gabriel E. J. Grant B. S. Halstead D. M. P. Mingos Chem. Soc. Rev. 1998 27 213
- (1998) Chem. Soc. Rev. , vol.27 , pp. 213
- Gabriel, C.¹ Gabriel, S.² Grant, E.J.³ Halstead, B.S.⁴ Mingos, D.M.P.⁵

34
- 79958117726
- Y. Loidreau T. Besson Tetrahedron 2011 67 4852
- (2011) Tetrahedron , vol.67 , pp. 4852
- Loidreau, Y.¹ Besson, T.²

35
- 67149105794
- C. Lamazzi A. Dreau C. Bufferne C. Flouzat P. Carlier R. ter Halle T. Besson Tetrahedron Lett. 2009 50 4502
- (2009) Tetrahedron Lett. , vol.50 , pp. 4502
- Lamazzi, C.¹ Dreau, A.² Bufferne, C.³ Flouzat, C.⁴ Carlier, P.⁵ Ter Halle, R.⁶ Besson, T.⁷

36
- 54049148488
- I. Nouira I. K. Kostakis C. Dubouilh E. Chosson M. Iannelli T. Besson Tetrahedron Lett. 2008 49 7033
- (2008) Tetrahedron Lett. , vol.49 , pp. 7033
- Nouira, I.¹ Kostakis, I.K.² Dubouilh, C.³ Chosson, E.⁴ Iannelli, M.⁵ Besson, T.⁶

37
- 17744371332
- C. Mésangeau S. Yous B. Pérès D. Lesieur T. Besson Tetrahedron Lett. 2005 46 2465
- (2005) Tetrahedron Lett. , vol.46 , pp. 2465
- Mésangeau, C.¹ Yous, S.² Pérès, B.³ Lesieur, D.⁴ Besson, T.⁵

38
- 0038738278
- Y. Wan M. Alterman M. Larhed A. Halberg J. Comb. Chem. 2003 5 82
- (2003) J. Comb. Chem. , vol.5 , pp. 82
- Wan, Y.¹ Alterman, M.² Larhed, M.³ Halberg, A.⁴

39
- 36749059482
- E. B. Wilson J. Chem. Phys. 1962 36 2232
- (1962) J. Chem. Phys. , vol.36 , pp. 2232
- Wilson, E.B.¹

40
- 0003824417
- in, Plenum Press, New York
- Chemical Applications of Atomic and Molecular Electrostatic Potentials, in P. Politzer, Plenum Press, New York, 1981
- (1981) Chemical Applications of Atomic and Molecular Electrostatic Potentials
- Politzer, P.¹

41
- 0000870268
- B. Galabov P. Bobadova-Parvanova J. Phys. Chem. A 1999 103 6793
- (1999) J. Phys. Chem. A , vol.103 , pp. 6793
- Galabov, B.¹ Bobadova-Parvanova, P.²

42
- 0037028199
- V. Dimitrova S. Ilieva B. Galabov J. Phys. Chem. A 2002 106 11801
- (2002) J. Phys. Chem. A , vol.106 , pp. 11801
- Dimitrova, V.¹ Ilieva, S.² Galabov, B.³

43
- 11444252304
- B. Galabov D. Cheshmedzhieva S. Ilieva B. Hadjieva J. Phys. Chem. A 2004 108 11457
- (2004) J. Phys. Chem. A , vol.108 , pp. 11457
- Galabov, B.¹ Cheshmedzhieva, D.² Ilieva, S.³ Hadjieva, B.⁴

44
- 33747390799
- B. Galabov S. Ilieva H. F. Schaefer III J. Org. Chem. 2006 71 6382
- (2006) J. Org. Chem. , vol.71 , pp. 6382
- Galabov, B.¹ Ilieva, S.² Schaefer Iii, H.F.³

45
- 48349084446
- B. Galabov V. Nikolova J. J. Wilke H. F. Schaefer III W. D. Allen J. Am. Chem. Soc. 2008 130 9887
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 9887
- Galabov, B.¹ Nikolova, V.² Wilke, J.J.³ Schaefer Iii, H.F.⁴ Allen, W.D.⁵

46
- 49149109637
- B. Galabov S. Ilieva B. Hadjieva B. Y. Atanasov H. F. Schaefer III J. Phys. Chem. A 2008 112 6700
- (2008) J. Phys. Chem. A , vol.112 , pp. 6700
- Galabov, B.¹ Ilieva, S.² Hadjieva, B.³ Atanasov, B.Y.⁴ Schaefer Iii, H.F.⁵

47
- 70350046691
- G. Koleva B. Galabov J. I. Wu H. F. Schaefer III P. V. R. Schleyer J. Am. Chem. Soc. 2009 131 14722
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 14722
- Koleva, G.¹ Galabov, B.² Wu, J.I.³ Schaefer Iii, H.F.⁴ Schleyer, P.V.R.⁵

48
- 0001436735
- J. S. Murray P. Politzer Chem. Phys. Lett. 1988 152 364
- (1988) Chem. Phys. Lett. , vol.152 , pp. 364
- Murray, J.S.¹ Politzer, P.²

49
- 0001607016
- T. Brinck J. S. Murray P. Politzer J. Org. Chem. 1991 56 5012
- (1991) J. Org. Chem. , vol.56 , pp. 5012
- Brinck, T.¹ Murray, J.S.² Politzer, P.³

50
- 0032558106
- C. H. Suresh S. R. Gadre J. Am. Chem. Soc. 1998 120 7049
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 7049
- Suresh, C.H.¹ Gadre, S.R.²

51
- 33847057299
- C. H. Suresh S. R. Gadre J. Phys. Chem. A 2007 111 710
- (2007) J. Phys. Chem. A , vol.111 , pp. 710
- Suresh, C.H.¹ Gadre, S.R.²

53
- 33846053175
- Y. Zhao D. G. Truhlar J. Phys. Chem. A 2006 110 13126
- (2006) J. Phys. Chem. A , vol.110 , pp. 13126
- Zhao, Y.¹ Truhlar, D.G.²

54
- 43049141516
- Y. Zhao D. G. Truhlar Theor. Chem. Acc. 2008 120 215
- (2008) Theor. Chem. Acc. , vol.120 , pp. 215
- Zhao, Y.¹ Truhlar, D.G.²

55
- 66349120487
- A. V. Marenich C. J. Cramer D. G. Truhlar J. Phys. Chem. B 2009 113 6378
- (2009) J. Phys. Chem. B , vol.113 , pp. 6378
- Marenich, A.V.¹ Cramer, C.J.² Truhlar, D.G.³

56
- 77949347282
- S. E. Wheeler K. N. Houk J. Chem. Theory Comput. 2010 6 395
- (2010) J. Chem. Theory Comput. , vol.6 , pp. 395
- Wheeler, S.E.¹ Houk, K.N.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.