SCOPUS 정보 검색 플랫폼

Volumn 67, Issue 12, 2011, Pages 2269-2278

Synthesis of 3-substituted benzo[g]isoquinoline-5,10-diones: A convenient one-pot Sonogashira coupling/iminoannulation procedure

(5) Van Aeken, Sam a Verbeeck, Stefan b Deblander, Jurgen a Maes, Bert U W b Abbaspour Tehrani, Kourosch a,b

a VRIJE UNIVERSITEIT BRUSSEL (Belgium)

b UNIVERSITY OF ANTWERP (Belgium)

Author keywords

Benzo g isoquinoline 5,10 diones; Iminoannulation; Naphthalene; Quinones; Sonogashira

Indexed keywords

2 AZA ANTHRAQUINONE; 3 ALKYNYL 1,4 DIMETHOXY 2 NAPHTHALDEHYDE; 3 ALKYNYL 2 NAPHTHYLCARBALDEHYDE; 3 BROMO 1,4 DIMETHOXY 2 NAPHTHALDEHYDE; 5,10 DIMETHOXYBENZO[G]ISOQUINOLINE; ACETYLENE; ALDEHYDE DERIVATIVE; ALKYNE; AMMONIA; ANTHRAQUINONE DERIVATIVE; AROMATIC COMPOUND; BENZENE DERIVATIVE; BENZO[F]INDENONE; BENZOQUINONE DERIVATIVE; CARBONIC ACID DERIVATIVE; CERIUM AMMONIUM NITRATE; CESIUM CARBONATE; COPPER; IMINE; ISOQUINOLINE; ISOQUINOLINE DERIVATIVE; NAPHTHALENE DERIVATIVE; NITRIC ACID DERIVATIVE; PALLADIUM; PHENYLACETYLENE; POTASSIUM CARBONATE; TERT BUTYLIMINE; UNCLASSIFIED DRUG;

ACIDIFICATION; ANNULATION REACTION; ARTICLE; BIOTRANSFORMATION; CATALYST; CHEMICAL STRUCTURE; CONTROLLED STUDY; CROSS COUPLING REACTION; CYCLIZATION; CYCLOADDITION; DEMETHYLATION; IMINOANNULATION; ONE POT SYNTHESIS; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; SONOGASHIRA REACTION; SUBSTITUTION REACTION;

EID: 79952191177 PISSN: 00404020 EISSN: None Source Type: Journal
DOI: 10.1016/j.tet.2011.01.074 Document Type: Article

Times cited : (13)

References (33)

1
- 16244379548
- J. Koyama, I. Morita, N. Kobayashi, T. Osakai, Y. Usuki, and M. Taniguchi Bioorg. Med. Chem. Lett. 15 2005 1079 1082
- (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 1079-1082
- Koyama, J.¹ Morita, I.² Kobayashi, N.³ Osakai, T.⁴ Usuki, Y.⁵ Taniguchi, M.⁶

2
- 0043123417
- I. Gomez-Monterrey, P. Campiglia, P. Grieco, M. Vittoria Diurno, A. Bolognese, P. La Colla, and E. Novellino Bioorg. Med. Chem. 11 2003 3769 3775
- (2003) Bioorg. Med. Chem. , vol.11 , pp. 3769-3775
- Gomez-Monterrey, I.¹ Campiglia, P.² Grieco, P.³ Vittoria Diurno, M.⁴ Bolognese, A.⁵ La Colla, P.⁶ Novellino, E.⁷

3
- 0032492663
- G. Bruckhardt, A. Walter, H. Triebel, K. Störl, H. Simon, J. Störl, A. Opitz, E. Roemer, and C. Zimmer Biochemistry 37 1998 4703 4711
- (1998) Biochemistry , vol.37 , pp. 4703-4711
- Bruckhardt, G.¹ Walter, A.² Triebel, H.³ Störl, K.⁴ Simon, H.⁵ Störl, J.⁶ Opitz, A.⁷ Roemer, E.⁸ Zimmer, C.⁹

4
- 0029016591
- L.A. Hazlehurst, A.P. Krapcho, and M.P. Hacker Cancer Lett. 91 1995 115 124
- (1995) Cancer Lett. , vol.91 , pp. 115-124
- Hazlehurst, L.A.¹ Krapcho, A.P.² Hacker, M.P.³

5
- 16244384650
- J. Tarasiuk, J. Mazerski, K. Tkaczyk-Gobis, and E. Borowski Eur. J. Med. Chem. 40 2005 321 328
- (2005) Eur. J. Med. Chem. , vol.40 , pp. 321-328
- Tarasiuk, J.¹ Mazerski, J.² Tkaczyk-Gobis, K.³ Borowski, E.⁴

6
- 3042855362
- J. Koyama, I. Morita, N. Kobayashi, T. Osaki, H. Hotta, J. Takayasu, H. Nishino, and H. Tokuda Cancer Lett. 212 2004 1 6
- (2004) Cancer Lett. , vol.212 , pp. 1-6
- Koyama, J.¹ Morita, I.² Kobayashi, N.³ Osaki, T.⁴ Hotta, H.⁵ Takayasu, J.⁶ Nishino, H.⁷ Tokuda, H.⁸

7
- 0022450027
- K.T. Potts, D. Bhattacharjee, and E.B. Walsh J. Org. Chem. 51 1986 2011 2021
- (1986) J. Org. Chem. , vol.51 , pp. 2011-2021
- Potts, K.T.¹ Bhattacharjee, D.² Walsh, E.B.³

8
- 56349121749
- J.A. Valderrama, P. Colonelli, D. Vásquez, M.F. González, J.A. Rodríguez, and C. Theoduloz Bioorg. Med. Chem. 16 2008 10172 10181
- (2008) Bioorg. Med. Chem. , vol.16 , pp. 10172-10181
- Valderrama, J.A.¹ Colonelli, P.² Vásquez, D.³ González, M.F.⁴ Rodríguez, J.A.⁵ Theoduloz, C.⁶

9
- 0034647754
- A. Opitz, E. Roemer, W. Haas, H. Görls, W. Werner, and U. Gräfe Tetrahedron 56 2000 5147 5155
- (2000) Tetrahedron , vol.56 , pp. 5147-5155
- Opitz, A.¹ Roemer, E.² Haas, W.³ Görls, H.⁴ Werner, W.⁵ Gräfe, U.⁶

10
- 0000231780
- G. Sartori, G. Casnati, F. Bigi, and P. Robles Tetrahedron Lett. 28 1987 1533 1536
- (1987) Tetrahedron Lett. , vol.28 , pp. 1533-1536
- Sartori, G.¹ Casnati, G.² Bigi, F.³ Robles, P.⁴

11
- 0023243093
- M. Wanatabe, E. Shinoda, Y. Shimizu, and S. Furukawa Tetrahedron 43 1987 5281 5286
- (1987) Tetrahedron , vol.43 , pp. 5281-5286
- Wanatabe, M.¹ Shinoda, E.² Shimizu, Y.³ Furukawa, S.⁴

12
- 1342282233
- A.-S. Rebstock, F. Mongin, F. Trécourt, and G. Quéguiner Org. Biomol. Chem. 2 2004 291 295
- (2004) Org. Biomol. Chem. , vol.2 , pp. 291-295
- Rebstock, A.-S.¹ Mongin, F.² Trécourt, F.³ Quéguiner, G.⁴

13
- 79952195976
- B. Kesteleyn, T. Nguyen Van, and N. De Kimpe Tetrahedron 55 1999 2092 2102
- (1999) Tetrahedron , vol.55 , pp. 2092-2102
- Kesteleyn, B.¹ Van, N.T.² De Kimpe, N.³

14
- 13644249110
- T. Nguyen Van, G. Verniest, S. Claessens, and N. De Kimpe Tetrahedron 61 2005 2295 2300
- (2005) Tetrahedron , vol.61 , pp. 2295-2300
- Van, N.T.¹ Verniest, G.² Claessens, S.³ De Kimpe, N.⁴

15
- 0037059480
- K.R. Roesch, and R.C. Larock J. Org. Chem. 67 2002 86 94
- (2002) J. Org. Chem. , vol.67 , pp. 86-94
- Roesch, K.R.¹ Larock, R.C.²

16
- 70449369054
- S. Roy, S. Roy, B. Neuenswander, D. Hill, and R.C. Larock J. Comb. Chem. 11 2009 1061 1065
- (2009) J. Comb. Chem. , vol.11 , pp. 1061-1065
- Roy, S.¹ Roy, S.² Neuenswander, B.³ Hill, D.⁴ Larock, R.C.⁵

17
- 0344391941
- S. Mondal, T. Nogami, N. Asao, and Y. Yamamoto J. Org. Chem. 68 2003 9496 9498
- (2003) J. Org. Chem. , vol.68 , pp. 9496-9498
- Mondal, S.¹ Nogami, T.² Asao, N.³ Yamamoto, Y.⁴

18
- 79952183762
- L. Syper, and J. Młochowski Synthesis 1983 747 752
- (1983) Synthesis , pp. 747-752
- Syper, L.¹ Młochowski, J.²

19
- 0141630547
- P. Magnus, K.S. Matthews, and V. Lynch Org. Lett. 5 2003 2181 2184
- (2003) Org. Lett. , vol.5 , pp. 2181-2184
- Magnus, P.¹ Matthews, K.S.² Lynch, V.³

20
- 0000618599
- F. Paul, J. Patt, and J.F. Hartwig Organometallics 14 1995 3030 3039
- (1995) Organometallics , vol.14 , pp. 3030-3039
- Paul, F.¹ Patt, J.² Hartwig, J.F.³

21
- 41049083367
- M. Van der Heiden, and H. Plenio Chem. Commun. 2007 972 974
- (2007) Chem. Commun. , pp. 972-974
- Van Der Heiden, M.¹ Plenio, H.²

22
- 0000629440
- T. Jeffery L.S. Liebeskind, Advances in Metal-Organic Chemistry Vol. 5 1996 JAI Greenwich 153 260
- (1996) Advances in Metal-Organic Chemistry , vol.5 , pp. 153-260
- Jeffery, T.¹

23
- 0028236671
- T. Jeffery, and J.-C. Galland Tetrahedron Lett. 35 1994 4103 4106
- (1994) Tetrahedron Lett. , vol.35 , pp. 4103-4106
- Jeffery, T.¹ Galland, J.-C.²

24
- 0030598098
- T. Jeffery Tetrahedron 52 1996 10113 10130
- (1996) Tetrahedron , vol.52 , pp. 10113-10130
- Jeffery, T.¹

25
- 0028334372
- T. Jeffery Tetrahedron Lett. 35 1994 3051 3954
- (1994) Tetrahedron Lett. , vol.35 , pp. 3051-3954
- Jeffery, T.¹

26
- 0035831163
- H.-F. Chow, C.-W. Wan, K.-H. Low, and Y.-Y. Yeung J. Org. Chem. 66 2001 1910 1913
- (2001) J. Org. Chem. , vol.66 , pp. 1910-1913
- Chow, H.-F.¹ Wan, C.-W.² Low, K.-H.³ Yeung, Y.-Y.⁴

27
- 0030605876
- J.-F. Nguefack, V. Bolitt, and D. Sinou Tetrahedron Lett. 37 1996 5527 5530
- (1996) Tetrahedron Lett. , vol.37 , pp. 5527-5530
- Nguefack, J.-F.¹ Bolitt, V.² Sinou, D.³

28
- 0034249671
- I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009 3066
- (2000) Chem. Rev. , vol.100 , pp. 3009-3066
- Beletskaya, I.P.¹ Cheprakov, A.V.²

29
- 0000570590
- L.S. Liebeskind, and M.S. South J. Org. Chem. 45 1980 5426 5429
- (1980) J. Org. Chem. , vol.45 , pp. 5426-5429
- Liebeskind, L.S.¹ South, M.S.²

30
- 0000913941
- R.C. Larock, and M.J. Doty J. Org. Chem. 58 1993 4579 4583
- (1993) J. Org. Chem. , vol.58 , pp. 4579-4583
- Larock, R.C.¹ Doty, M.J.²

31
- 79952187994
- A. Chandra, B. Singh, S. Upadhyay, and R.M. Singh Tetrahedron 64 2008 11608 11685
- (2008) Tetrahedron , vol.64 , pp. 11608-11685
- Chandra, A.¹ Singh, B.² Upadhyay, S.³ Singh, R.M.⁴

32
- 66449128802
- M. Alfonsi, M. Dell'Acqua, D. Facoetti, A. Arcadi, G. Abbiati, and E. Rossi Eur. J. Org. Chem. 2009 2852 2862
- (2009) Eur. J. Org. Chem. , pp. 2852-2862
- Alfonsi, M.¹ Dell'Acqua, M.² Facoetti, D.³ Arcadi, A.⁴ Abbiati, G.⁵ Rossi, E.⁶

33
- 77953306636
- For examples of oxidative demethylations with CAN see: V. Sridharan, and J.C. Menéndez Chem. Rev. 110 2010 3805 3849
- (2010) Chem. Rev. , vol.110 , pp. 3805-3849
- Sridharan, V.¹ Menéndez, J.C.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.