SCOPUS 정보 검색 플랫폼

Chemical Communications

Volumn 51, Issue 96, 2015, Pages 17166-17169

Cu-catalyzed transannulation reaction of pyridotriazoles: General access to fused polycyclic indolizines

(2) Shi, Yi a Gevorgyan, Vladimir a

a UNIVERSITY OF ILLINOIS AT CHICAGO (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; INDOLIZINE DERIVATIVE; PYRIDOTRIAZOLE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; CYCLOADDITION; DESILYLATION; ELECTROPHILICITY; NUCLEOPHILICITY; REACTION ANALYSIS;

EID: 84948131309 PISSN: 13597345 EISSN: 1364548X Source Type: Journal
DOI: 10.1039/c5cc07598j Document Type: Article

Times cited : (74)

References (67)

1
- 84872833141
- A. V. Gulevich V. Gevorgyan Angew. Chem., Int. Ed. 2013 52 1371
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 1371
- Gulevich, A.V.¹ Gevorgyan, V.²

2
- 84903188730
- For reports on pyridotriazoles, see
- H. M. L. Davies J. S. Alford Chem. Soc. Rev. 2014 43 5151
- (2014) Chem. Soc. Rev. , vol.43 , pp. 5151
- Davies, H.M.L.¹ Alford, J.S.²

3
- 34347204116
- S. Chuprakov F. Hwang V. Gevorgyan Angew. Chem., Int. Ed. 2007 46 4757
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 4757
- Chuprakov, S.¹ Hwang, F.² Gevorgyan, V.³

4
- 35948975670
- S. Chuprakov V. Gevorgyan Org. Lett. 2007 9 4463
- (2007) Org. Lett. , vol.9 , pp. 4463
- Chuprakov, S.¹ Gevorgyan, V.²

5
- 84917708585
- Y. Shi A. V. Gulevich V. Gevorgyan Angew. Chem., Int. Ed. 2014 53 14191
- (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 14191
- Shi, Y.¹ Gulevich, A.V.² Gevorgyan, V.³

6
- 84923207216
- For review, see
- V. Helan A. V. Gulevich V. Gevorgyan Chem. Sci. 2015 6 1928
- (2015) Chem. Sci. , vol.6 , pp. 1928
- Helan, V.¹ Gulevich, A.V.² Gevorgyan, V.³

7
- 84855990688
- For transannulation reactions of N-sulfonyl triazoles, see
- B. Chattopadhyay V. Gevorgyan Angew. Chem., Int. Ed. 2012 51 862
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 862
- Chattopadhyay, B.¹ Gevorgyan, V.²

8
- 57349191194
- T. Horneff S. Chuprakov N. Chernyak V. Gevorgyan V. V. Fokin J. Am. Chem. Soc. 2008 130 14972
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14972
- Horneff, T.¹ Chuprakov, S.² Chernyak, N.³ Gevorgyan, V.⁴ Fokin, V.V.⁵

9
- 61849183666
- T. Miura M. Yamauchi M. Murakami Chem. Commun. 2009 1470
- (2009) Chem. Commun. , pp. 1470
- Miura, T.¹ Yamauchi, M.² Murakami, M.³

10
- 79960178492
- B. Chattopadhyay V. Gevorgyan Org. Lett. 2011 13 3746
- (2011) Org. Lett. , vol.13 , pp. 3746
- Chattopadhyay, B.¹ Gevorgyan, V.²

11
- 84875727243
- B. T. Parr S. A. Green H. M. L. Davies J. Am. Chem. Soc. 2013 135 4716
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 4716
- Parr, B.T.¹ Green, S.A.² Davies, H.M.L.³

12
- 84877279503
- J. E. Spangler H. M. L. Davies J. Am. Chem. Soc. 2013 135 6802
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 6802
- Spangler, J.E.¹ Davies, H.M.L.²

13
- 84882262173
- J. S. Alford J. E. Spangler H. M. L. Davies J. Am. Chem. Soc. 2013 135 11712
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 11712
- Alford, J.S.¹ Spangler, J.E.² Davies, H.M.L.³

14
- 84882272975
- B. T. Parr H. M. L. Davies Angew. Chem., Int. Ed. 2013 52 10044
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 10044
- Parr, B.T.¹ Davies, H.M.L.²

15
- 84872864965
- M. Zibinsky V. V. Fokin Angew. Chem., Int. Ed. 2013 52 1507
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 1507
- Zibinsky, M.¹ Fokin, V.V.²

16
- 84875750598
- S. Chuprakov S. W. Kwok V. V. Fokin J. Am. Chem. Soc. 2013 135 4652
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 4652
- Chuprakov, S.¹ Kwok, S.W.² Fokin, V.V.³

17
- 84884494498
- T. Miura T. Tanaka K. Hiraga S. G. Stewart M. Murakami J. Am. Chem. Soc. 2013 135 13652
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 13652
- Miura, T.¹ Tanaka, T.² Hiraga, K.³ Stewart, S.G.⁴ Murakami, M.⁵

18
- 84880004562
- T. Miura K. Hiraga T. Biyajima T. Nakamuro M. Murakami Org. Lett. 2013 15 3298
- (2013) Org. Lett. , vol.15 , pp. 3298
- Miura, T.¹ Hiraga, K.² Biyajima, T.³ Nakamuro, T.⁴ Murakami, M.⁵

19
- 84875701371
- E. E. Schultz R. Sarpong J. Am. Chem. Soc. 2013 135 4696
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 4696
- Schultz, E.E.¹ Sarpong, R.²

20
- 84886304031
- Y. Shi V. Gevorgyan Org. Lett. 2013 15 5394
- (2013) Org. Lett. , vol.15 , pp. 5394
- Shi, Y.¹ Gevorgyan, V.²

21
- 84894115779
- T. Miura Y. Funakoshi M. Murakami J. Am. Chem. Soc. 2014 136 2272
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 2272
- Miura, T.¹ Funakoshi, Y.² Murakami, M.³

22
- 84898739783
- C. Kim S. Park D. Eom B. Seo P. H. Lee Org. Lett. 2014 16 1900
- (2014) Org. Lett. , vol.16 , pp. 1900
- Kim, C.¹ Park, S.² Eom, D.³ Seo, B.⁴ Lee, P.H.⁵

23
- 84899995236
- J. Yang C. Zhu X. Tang M. Shi Angew. Chem., Int. Ed. 2014 53 5142
- (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 5142
- Yang, J.¹ Zhu, C.² Tang, X.³ Shi, M.⁴

24
- 84901617584
- H. Shang Y. Wang Y. Tian J. Feng Y. Tang Angew. Chem., Int. Ed. 2014 53 5662
- (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 5662
- Shang, H.¹ Wang, Y.² Tian, Y.³ Feng, J.⁴ Tang, Y.⁵

25
- 84903268945
- K. Chen Z.-Z. Zhu Y.-S. Zhang X.-Y. Tang M. Shi Angew. Chem., Int. Ed. 2014 53 6645
- (2014) Angew. Chem., Int. Ed. , vol.53 , pp. 6645
- Chen, K.¹ Zhu, Z.-Z.² Zhang, Y.-S.³ Tang, X.-Y.⁴ Shi, M.⁵

26
- 84904543404
- B. Rajagopal C.-H. Chou C.-C. Chung P.-C. Lin Org. Lett. 2014 16 3752
- (2014) Org. Lett. , vol.16 , pp. 3752
- Rajagopal, B.¹ Chou, C.-H.² Chung, C.-C.³ Lin, P.-C.⁴

27
- 84904565847
- R.-Q. Ran J. He S.-D. Xiu K.-B. Wang C.-Y. Li Org. Lett. 2014 16 3704
- (2014) Org. Lett. , vol.16 , pp. 3704
- Ran, R.-Q.¹ He, J.² Xiu, S.-D.³ Wang, K.-B.⁴ Li, C.-Y.⁵

28
- 84903187740
- F. Medina C. Besnard J. Lacour Org. Lett. 2014 16 3232
- (2014) Org. Lett. , vol.16 , pp. 3232
- Medina, F.¹ Besnard, C.² Lacour, J.³

29
- 84936802854
- For other reactions of N-sulfonyl triazoles, see
- V. N. G. Lindsay H. M.-F. Viart R. Sarpong J. Am. Chem. Soc. 2015 137 8368
- (2015) J. Am. Chem. Soc. , vol.137 , pp. 8368
- Lindsay, V.N.G.¹ Viart, H.M.-F.² Sarpong, R.³

30
- 77950337980
- N. Grimster L. Zhang V. V. Fokin J. Am. Chem. Soc. 2010 132 2510
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 2510
- Grimster, N.¹ Zhang, L.² Fokin, V.V.³

31
- 72449165436
- S. Chuprakov S. W. Kwok L. Zhang L. Lercher V. V. Fokin J. Am. Chem. Soc. 2009 131 18034
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 18034
- Chuprakov, S.¹ Kwok, S.W.² Zhang, L.³ Lercher, L.⁴ Fokin, V.V.⁵

32
- 84866369102
- N. Selander B. T. Worrell S. Chuprakov S. Velaparthi V. V. Fokin J. Am. Chem. Soc. 2012 134 14670
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 14670
- Selander, N.¹ Worrell, B.T.² Chuprakov, S.³ Velaparthi, S.⁴ Fokin, V.V.⁵

33
- 84892181640
- S. Chuprakov B. T. Worrell N. Selander R. K. Sit V. V. Fokin J. Am. Chem. Soc. 2014 136 195
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 195
- Chuprakov, S.¹ Worrell, B.T.² Selander, N.³ Sit, R.K.⁴ Fokin, V.V.⁵

34
- 79960049239
- S. Chuprakov J. A. Malik M. Zibinsky V. V. Fokin J. Am. Chem. Soc. 2011 133 10352
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 10352
- Chuprakov, S.¹ Malik, J.A.² Zibinsky, M.³ Fokin, V.V.⁴

35
- 84870937646
- J. S. Alford H. M. L. Davies Org. Lett. 2012 14 6020
- (2012) Org. Lett. , vol.14 , pp. 6020
- Alford, J.S.¹ Davies, H.M.L.²

36
- 84855684122
- T. Muira T. Biyajima T. Fujii M. Murakami J. Am. Chem. Soc. 2012 134 194
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 194
- Muira, T.¹ Biyajima, T.² Fujii, T.³ Murakami, M.⁴

37
- 84875750924
- T. Miura T. Tanaka T. Biyajima A. Yada M. Murakami Angew. Chem., Int. Ed. 2013 52 3883
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 3883
- Miura, T.¹ Tanaka, T.² Biyajima, T.³ Yada, A.⁴ Murakami, M.⁵

38
- 84867833006
- T. Miura Y. Funakoshi M. Morimoto T. Biyajima M. Murakami J. Am. Chem. Soc. 2012 134 17440
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 17440
- Miura, T.¹ Funakoshi, Y.² Morimoto, M.³ Biyajima, T.⁴ Murakami, M.⁵

39
- 84871977552
- N. Selander B. T. Worrell V. V. Fokin Angew. Chem., Int. Ed. 2012 51 13054
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 13054
- Selander, N.¹ Worrell, B.T.² Fokin, V.V.³

40
- 84896950279
- A. Boyer Org. Lett. 2014 16 1660
- (2014) Org. Lett. , vol.16 , pp. 1660
- Boyer, A.¹

41
- 84899004056
- D. J. Jung H. J. Jeon J. H. Kim Y. Kim S. Lee Org. Lett. 2014 16 2208
- (2014) Org. Lett. , vol.16 , pp. 2208
- Jung, D.J.¹ Jeon, H.J.² Kim, J.H.³ Kim, Y.⁴ Lee, S.⁵

42
- 84899825951
- D. Yadagiri P. Anbarasan Org. Lett. 2014 16 2510
- (2014) Org. Lett. , vol.16 , pp. 2510
- Yadagiri, D.¹ Anbarasan, P.²

43
- 84900836715
- T. Miura Y. Funakoshi T. Tanaka M. Murakami Org. Lett. 2014 16 2760
- (2014) Org. Lett. , vol.16 , pp. 2760
- Miura, T.¹ Funakoshi, Y.² Tanaka, T.³ Murakami, M.⁴

44
- 84906238964
- T. Miura T. Nakamuro K. Hiraga M. Murakami Chem. Commun. 2014 50 10474
- (2014) Chem. Commun. , vol.50 , pp. 10474
- Miura, T.¹ Nakamuro, T.² Hiraga, K.³ Murakami, M.⁴

45
- 84909990955
- T. Miura T. Nakamuro C.-J. Liang M. Murakami J. Am. Chem. Soc. 2014 136 15905
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 15905
- Miura, T.¹ Nakamuro, T.² Liang, C.-J.³ Murakami, M.⁴

46
- 84938902631
- T. Miura, Y. Fujimoto, Y. Funakoshi and M. Murakami, Angew. Chem., Int. Ed., 2015 54 9967 9970
- (2015) Angew. Chem., Int. Ed. , vol.54 , pp. 9967-9970
- Miura, T.¹ Fujimoto, Y.² Funakoshi, Y.³ Murakami, M.⁴

47
- 84863081974
- B. Liu Z. Wang N. Wu M. Li J. You J. Lan Chem.-Eur. J. 2012 18 1599
- (2012) Chem.-Eur. J. , vol.18 , pp. 1599
- Liu, B.¹ Wang, Z.² Wu, N.³ Li, M.⁴ You, J.⁵ Lan, J.⁶

48
- 84896546003
- Y. Wang A. V. Gulevich V. Gevorgyan Chem.-Eur. J. 2013 19 15836
- (2013) Chem.-Eur. J. , vol.19 , pp. 15836
- Wang, Y.¹ Gulevich, A.V.² Gevorgyan, V.³

49
- 84908405187
- See ESI, for details Alternatively, fused indolizines can be accessed via direct [3+2] cyclization of pyridinium salts with acrylates.
- D. U. Ganihigama S. Sureram S. Sangher P. Hongmanee T. Aree C. Mahidol S. Ruchirawat P. Kittakoop Eur. J. Med. Chem. 2015 89 1
- (2015) Eur. J. Med. Chem. , vol.89 , pp. 1
- Ganihigama, D.U.¹ Sureram, S.² Sangher, S.³ Hongmanee, P.⁴ Aree, T.⁵ Mahidol, C.⁶ Ruchirawat, S.⁷ Kittakoop, P.⁸

50
- 0033745431
- L. Zhang F. Liang L. Sun Y. Hu H. Hu Synthesis 2000 1733
- (2000) Synthesis , pp. 1733
- Zhang, L.¹ Liang, F.² Sun, L.³ Hu, Y.⁴ Hu, H.⁵

51
- 84876253135
- H. Hu J. Feng Y. Zhu N. Gu Y. Kan RSC Adv. 2012 2 8637
- (2012) RSC Adv. , vol.2 , pp. 8637
- Hu, H.¹ Feng, J.² Zhu, Y.³ Gu, N.⁴ Kan, Y.⁵

52
- 33846369081
- However, cyclization of meta-substituted pyridinium salt is not selective. 7b Attempts on employment of alkynyltriazole possessing ether tether were not successful For less efficient construction of 3,5-disubstituted indolizines via a cycloisomerization approach, see
- Y. Liu H.-Y. Hu Q.-J. Liu H.-W. Hu J.-H. Xu Tetrahedron 2007 63 2024
- (2007) Tetrahedron , vol.63 , pp. 2024
- Liu, Y.¹ Hu, H.-Y.² Liu, Q.-J.³ Hu, H.-W.⁴ Xu, J.-H.⁵

53
- 0035819945
- A. V. Kel'in A. W. Sromek V. Gevorgyan J. Am. Chem. Soc. 2001 123 2074
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 2074
- Kel'In, A.V.¹ Sromek, A.W.² Gevorgyan, V.³

54
- 84872295876
- For the Cu-catalyzed reactions involving copper carbene intermediates, see
- M. Arisawa Y. Fujii H. Kato H. Fukuda T. Matsumoto M. Ito H. Abe Y. Ito S. Shuto Angew. Chem., Int. Ed. 2013 52 1003
- (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 1003
- Arisawa, M.¹ Fujii, Y.² Kato, H.³ Fukuda, H.⁴ Matsumoto, T.⁵ Ito, M.⁶ Abe, H.⁷ Ito, Y.⁸ Shuto, S.⁹

55
- 4544224672
- A. Suárez G. Fu Angew. Chem., Int. Ed. 2004 43 3580
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3580
- Suárez, A.¹ Fu, G.²

56
- 34248531594
- B. Liu S.-F. Zhu W. Zhang C. Chen Q.-L. Zhou J. Am. Chem. Soc. 2007 129 5834
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 5834
- Liu, B.¹ Zhu, S.-F.² Zhang, W.³ Chen, C.⁴ Zhou, Q.-L.⁵

57
- 77957204725
- J. Barluenga G. Lonzi L. Riesgo L. A. López M. Tomás J. Am. Chem. Soc. 2010 132 13200
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 13200
- Barluenga, J.¹ Lonzi, G.² Riesgo, L.³ López, L.A.⁴ Tomás, M.⁵

58
- 78349243665
- E. Lourdusamy L. Yao C.-M. Park Angew. Chem., Int. Ed. 2010 49 7963
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 7963
- Lourdusamy, E.¹ Yao, L.² Park, C.-M.³

59
- 79251568604
- Q. Xiao Y. Xia H. Li Y. Zhang J. Wang Angew. Chem., Int. Ed. 2011 50 1114
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 1114
- Xiao, Q.¹ Xia, Y.² Li, H.³ Zhang, Y.⁴ Wang, J.⁵

60
- 79952123914
- L. Zhou Y. Shi Q. Xiao Y. Liu F. Ye Y. Zhang J. Wang Org. Lett. 2011 13 968
- (2011) Org. Lett. , vol.13 , pp. 968
- Zhou, L.¹ Shi, Y.² Xiao, Q.³ Liu, Y.⁴ Ye, F.⁵ Zhang, Y.⁶ Wang, J.⁷

61
- 80054719501
- F. Ye Y. Shi L. Zhou Q. Xiao Y. Zhang J. Wang Org. Lett. 2011 13 5020
- (2011) Org. Lett. , vol.13 , pp. 5020
- Ye, F.¹ Shi, Y.² Zhou, L.³ Xiao, Q.⁴ Zhang, Y.⁵ Wang, J.⁶

62
- 79952611097
- X. Zhao G. Wu Y. Zhang J. Wang J. Am. Chem. Soc. 2011 133 3296
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 3296
- Zhao, X.¹ Wu, G.² Zhang, Y.³ Wang, J.⁴

63
- 84867834201
- R. Liu M. Zhang G. Winston-McPherson W. Tang Chem. Commun. 2013 49 4376
- (2013) Chem. Commun. , vol.49 , pp. 4376
- Liu, R.¹ Zhang, M.² Winston-McPherson, G.³ Tang, W.⁴

64
- 84911879203
- For review, see
- M. L. Hossain F. Ye Z. Liu Y. Xia Y. Shi L. Zhou Y. Zhang J. Wang J. Org. Chem. 2014 79 8689
- (2014) J. Org. Chem. , vol.79 , pp. 8689
- Hossain, M.L.¹ Ye, F.² Liu, Z.³ Xia, Y.⁴ Shi, Y.⁵ Zhou, L.⁶ Zhang, Y.⁷ Wang, J.⁸

65
- 84866666954
- For aza-Nazarov cyclization reaction on a pyridine ring, see
- X. Zhao Y. Zhang J. Wang Chem. Commun. 2012 48 10162
- (2012) Chem. Commun. , vol.48 , pp. 10162
- Zhao, X.¹ Zhang, Y.² Wang, J.³

66
- 80051709413
- R. R. Naredla C. Zheng S. O. Nilsson Lill D. A. Klumpp J. Am. Chem. Soc. 2011 133 13169
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 13169
- Naredla, R.R.¹ Zheng, C.² Nilsson Lill, S.O.³ Klumpp, D.A.⁴

67
- 84921280311
- I. Karthikeyan D. Arunprasath G. Sekar Chem. Commun. 2015 51 1701
- (2015) Chem. Commun. , vol.51 , pp. 1701
- Karthikeyan, I.¹ Arunprasath, D.² Sekar, G.³

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