SCOPUS 정보 검색 플랫폼

Volumn , Issue 19, 2007, Pages 2995-2998

Preparation of unsaturated aminonitriles from the aza-Morita-Baylis-Hillman reactions of aldimines with penta-2,4-dienenitrile

(2) Clary, Kristen N a Back, Thomas G a

a UNIVERSITY OF CALGARY (Canada)

Author keywords

Aza Morita Baylis Hillman reaction; Conjugated diene; N (phenylsulfonyl)aldimines; Penta 2,4 dienenitrile; Unsaturated aminonitriles

Indexed keywords

ALDIMINE DERIVATIVE; AMINONITRILE DERIVATIVE; IMINE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 37349106811 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-990886 Document Type: Article

Times cited : (18)

References (45)

1
- 0001461985
- (a) Morita, K.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815.
- (1968) Bull. Chem. Soc. Jpn , vol.41 , pp. 2815
- Morita, K.¹ Suzuki, Z.² Hirose, H.³

2
- 37349070220
- Morita, K. JP 43003364, 1968; Chem. Abstr. 1968, 69, 58828s.
- (b) Morita, K. JP 43003364, 1968; Chem. Abstr. 1968, 69, 58828s.

3
- 37349064995
- Baylis, A. B.; Hillman, M. E. D. DE 2,155,113, 1972; Chem. Abstr. 1972, 77, 34174q.
- (c) Baylis, A. B.; Hillman, M. E. D. DE 2,155,113, 1972; Chem. Abstr. 1972, 77, 34174q.

4
- 0037366617
- For reviews, see: a
- For reviews, see: (a) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
- (2003) Chem. Rev , vol.103 , pp. 811
- Basavaiah, D.¹ Rao, A.J.² Satyanarayana, T.³

5
- 0342419508
- (b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
- (1996) Tetrahedron , vol.52 , pp. 8001
- Basavaiah, D.¹ Rao, P.D.² Hyma, R.S.³

6
- 0000892247
- (c) Ciganek, E. Org. React. 1997, 51, 201.
- (1997) Org. React , vol.51 , pp. 201
- Ciganek, E.¹

7
- 0034283585
- (d) Langer, P. Angew. Chem. Int. Ed. 2000, 39, 3049.
- (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3049
- Langer, P.¹

8
- 4744362831
- (e) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
- (1988) Tetrahedron , vol.44 , pp. 4653
- Drewes, S.E.¹ Roos, G.H.P.²

9
- 34347262098
- (f) Masson, G.; Housseman, C.; Zhu, J. Angew. Chem. Int. Ed. 2007, 46, 4614.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 4614
- Masson, G.¹ Housseman, C.² Zhu, J.³

10
- 34347355605
- (g) Shi, Y.-L.; Shi. M. Eur. J. Org. Chem. 2007, 2905.
- (2007) Eur. J. Org. Chem , pp. 2905
- Shi, Y.-L.¹ Shi, M.²

11
- 0000077082
- For the first report of the aza-MBH reaction, see: a
- For the first report of the aza-MBH reaction, see: (a) Perlmutter, P.; Teo, C. C. Tetrahedron Lett. 1984, 25, 5951.
- (1984) Tetrahedron Lett , vol.25 , pp. 5951
- Perlmutter, P.¹ Teo, C.C.²

12
- 28844451041
- For other selected examples, see: b
- For other selected examples, see: (b) Buskens, P.; Klankermayer, J.; Leitner, W. J. Am. Chem. Soc. 2005, 127, 16762.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 16762
- Buskens, P.¹ Klankermayer, J.² Leitner, W.³

13
- 0347763335
- (c) Xu, Y.-M.; Shi, M. J. Org. Chem. 2004, 69, 417.
- (2004) J. Org. Chem , vol.69 , pp. 417
- Xu, Y.-M.¹ Shi, M.²

14
- 0038278402
- (d) Shi, M.; Xu, Y.-M. J. Org. Chem. 2003, 68, 4784.
- (2003) J. Org. Chem , vol.68 , pp. 4784
- Shi, M.¹ Xu, Y.-M.²

15
- 0037124397
- (e) Shi, M.; Zhao, G.-L. Tetrahedron Lett. 2002, 43, 4499.
- (2002) Tetrahedron Lett , vol.43 , pp. 4499
- Shi, M.¹ Zhao, G.-L.²

16
- 0037049187
- (f) Shi, M.; Zhao, G.-L. Tetrahedron Lett. 2002, 43, 9171.
- (2002) Tetrahedron Lett , vol.43 , pp. 9171
- Shi, M.¹ Zhao, G.-L.²

17
- 23744483102
- (g) Sun, S.; Zhang, Q.; Liu, Q.; Kang, J.; Yin, Y.; Li, D.; Dong, D. Tetrahedron Lett. 2005, 46, 6271.
- (2005) Tetrahedron Lett , vol.46 , pp. 6271
- Sun, S.¹ Zhang, Q.² Liu, Q.³ Kang, J.⁴ Yin, Y.⁵ Li, D.⁶ Dong, D.⁷

18
- 0037053852
- (h) Azizi, N.; Saidi, M. R. Tetrahedron Lett. 2002, 43, 4305.
- (2002) Tetrahedron Lett , vol.43 , pp. 4305
- Azizi, N.¹ Saidi, M.R.²

19
- 0032580401
- (i) Richter, H.; Jung, G. Tetrahedron Lett. 1998, 39, 2729.
- (1998) Tetrahedron Lett , vol.39 , pp. 2729
- Richter, H.¹ Jung, G.²

20
- 0242617763
- (j) Génisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem. Soc., Perkin Trans. 1 1996, 2869.
- (1996) J. Chem. Soc., Perkin Trans. 1 , pp. 2869
- Génisson, Y.¹ Massardier, C.² Gautier-Luneau, I.³ Greene, A.E.⁴

21
- 0001639550
- (k) Campi, E. M.; Holmes, A.; Perlmutter, P.; Teo, C. C. Aust. J. Chem. 1995, 48, 1535.
- (1995) Aust. J. Chem , vol.48 , pp. 1535
- Campi, E.M.¹ Holmes, A.² Perlmutter, P.³ Teo, C.C.⁴

22
- 21844523557
- (l) Cyrener, J.; Burger, K. Monatsh. Chem. 1995, 126, 319.
- (1995) Monatsh. Chem , vol.126 , pp. 319
- Cyrener, J.¹ Burger, K.²

23
- 0001266408
- (m) Bertenshaw, S.; Kahn, M. Tetrahedron Lett. 1989, 30, 2731.
- (1989) Tetrahedron Lett , vol.30 , pp. 2731
- Bertenshaw, S.¹ Kahn, M.²

24
- 20544446924
- Back, T. G.; Rankic, D. A.; Sorbetti, J. M.; Wulff, J. E. Org. Lett. 2005, 7, 2377.
- (2005) Org. Lett , vol.7 , pp. 2377
- Back, T.G.¹ Rankic, D.A.² Sorbetti, J.M.³ Wulff, J.E.⁴

25
- 34247562659
- Sorbetti, J. M.; Clary, K. N.; Rankic, D. A.; Wulff, J. E.; Parvez, M.; Back, T. G. J. Org. Chem. 2007, 72, 3326.
- (2007) J. Org. Chem , vol.72 , pp. 3326
- Sorbetti, J.M.¹ Clary, K.N.² Rankic, D.A.³ Wulff, J.E.⁴ Parvez, M.⁵ Back, T.G.⁶

26
- 0037423248
- For the use of HQD in MBH reactions, see: a
- For the use of HQD in MBH reactions, see: (a) Aggarwal, V. K.; Emme, I.; Fulford, S. Y. J. Org. Chem. 2003, 68, 692.
- (2003) J. Org. Chem , vol.68 , pp. 692
- Aggarwal, V.K.¹ Emme, I.² Fulford, S.Y.³

27
- 0026076065
- (b) Bode, M. L.; Kaye, P. T. Tetrahedron Lett. 1991, 32, 5611.
- (1991) Tetrahedron Lett , vol.32 , pp. 5611
- Bode, M.L.¹ Kaye, P.T.²

28
- 84948256942
- (c) Ameer, F.; Drewes, S. E.; Freese, S.; Kaye, P. T. Synth. Commun. 1988, 18, 495.
- (1988) Synth. Commun , vol.18 , pp. 495
- Ameer, F.¹ Drewes, S.E.² Freese, S.³ Kaye, P.T.⁴

29
- 84947191160
- (d) Drewes, S. E.; Freese, S. D.; Emslie, N. D.; Roos, G. H. P. Synth. Commun. 1988, 18, 1565.
- (1988) Synth. Commun , vol.18 , pp. 1565
- Drewes, S.E.¹ Freese, S.D.² Emslie, N.D.³ Roos, G.H.P.⁴

30
- 28944436138
- Shi, Y.-L.; Shi, M. Tetrahedron 2006, 62, 461.
- (2006) Tetrahedron , vol.62 , pp. 461
- Shi, Y.-L.¹ Shi, M.²

31
- 0032546214
- Zhang, T. Y.; O'Toole, J. C.; Dunigan, J. M. Tetrahedron Lett. 1998, 39, 1461.
- (1998) Tetrahedron Lett , vol.39 , pp. 1461
- Zhang, T.Y.¹ O'Toole, J.C.² Dunigan, J.M.³

32
- 0015529120
- Isbell, A. F.; Berry, J. P.; Tansey, L. W. J. Org. Chem. 1972, 37, 4399.
- (1972) J. Org. Chem , vol.37 , pp. 4399
- Isbell, A.F.¹ Berry, J.P.² Tansey, L.W.³

33
- 37349128420
- Preparation of Penta-2,4-dienenitrile (5) Potassium tert-butoxide (11.76 g, 104.8 mmol) in anhydrous THF (150 mL) was added dropwise to diethyl cyanomethylphosphonate (16.95 g, 95.76 mmol) in anhydrous THF (180 mL) at-78°C After 30 min, freshly distilled acrolein (6.00 g, 108 mmol) was added dropwise. The reaction mixture was stirred for 20 min and then warmed to r.t. and quenched with sat. aq NH4Cl solution. The solution was extracted with Et2O, washed with brine and H2O, and dried (MgSO4, The combined organic layers were concentrated on a rotary evaporator at r.t. and the residue was chromatographed on neutral alumina (hexanes-Et2O, 3:1) to afford 5 (3.974 g, 53, as a mixture of E/Z isomers (80:20, determined by NMR integration, 1H NMR (300 MHz, CDCl3, δ (E-isomer, 7.00 (dd, J, 15.9, 10.8 Hz, 1 H, 6.42 (dt, J, 16.9, 10.8 Hz, 1 H, 5.61 d
- 3): δ (E-isomer) = 7.00 (dd, J = 15.9, 10.8 Hz, 1 H), 6.42 (dt, J = 16.9, 10.8 Hz, 1 H), 5.61 (d, J = 16.9 Hz, 1 H), 5.55 (d, J = 10.2 Hz, 1 H); δ (Z-isomer) = 7.24 (d, J = 6.7 Hz, 1 H), 7.17 (d, J = 7.2 Hz, 1 H), 6.83 (dt, J = 10.3, 5.1 Hz, 1 H).

34
- 0037423248
- For the promotive effects of alcohols and related additives, see: a
- For the promotive effects of alcohols and related additives, see: (a) Aggarwal, V. K.; Emme, I.; Fulford, S. Y. J. Org. Chem. 2003, 68, 692.
- (2003) J. Org. Chem , vol.68 , pp. 692
- Aggarwal, V.K.¹ Emme, I.² Fulford, S.Y.³

35
- 0037169021
- (b) Aggarwal, V. K.; Dean, D. K.; Mereu, A.; Williams, R. J. Org. Chem. 2002, 67, 510.
- (2002) J. Org. Chem , vol.67 , pp. 510
- Aggarwal, V.K.¹ Dean, D.K.² Mereu, A.³ Williams, R.⁴

36
- 0013308184
- (c) Cai, J.; Zhou, Z.; Zhao, G.; Tang, C. Org. Lett. 2002, 4, 4723.
- (2002) Org. Lett , vol.4 , pp. 4723
- Cai, J.¹ Zhou, Z.² Zhao, G.³ Tang, C.⁴

37
- 0345681827
- (d) Grainger, R. S.; Leadbeater, N. E.; Pàmies, A. M. Catal. Commun. 2002, 3, 449.
- (2002) Catal. Commun , vol.3 , pp. 449
- Grainger, R.S.¹ Leadbeater, N.E.² Pàmies, A.M.³

38
- 0035838860
- (e) Yu, C.; Liu, B.; Hu, L. J. Org. Chem. 2001, 66, 5413.
- (2001) J. Org. Chem , vol.66 , pp. 5413
- Yu, C.¹ Liu, B.² Hu, L.³

39
- 0034719742
- (f) Yamada, Y. M. A.; Ikegami, S. Tetrahedron Lett. 2000, 41, 2165.
- (2000) Tetrahedron Lett , vol.41 , pp. 2165
- Yamada, Y.M.A.¹ Ikegami, S.²

40
- 0034026611
- (g) Basavaiah, D.; Krishnamacharyulu, M.; Rao, A. J. Synth. Commun. 2000, 30, 2061.
- (2000) Synth. Commun , vol.30 , pp. 2061
- Basavaiah, D.¹ Krishnamacharyulu, M.² Rao, A.J.³

41
- 3242736633
- (h) Basavaiah, D.; Rao, A. J.; Krishnamacharyulu, M. ARKIVOC 2002, (vii), 136.
- (2002) ARKIVOC , vol.7 , pp. 136
- Basavaiah, D.¹ Rao, A.J.² Krishnamacharyulu, M.³

42
- 0027974067
- (i) Augé, J.; Lubin, N.; Lubineau, A. Tetrahedron Lett. 1994, 35, 7947.
- (1994) Tetrahedron Lett , vol.35 , pp. 7947
- Augé, J.¹ Lubin, N.² Lubineau, A.³

43
- 84948256942
- (j) Ameer, F.; Drewes, S. E.; Freese, S.; Kaye, P. T. Synth. Commun. 1988, 18, 495.
- (1988) Synth. Commun , vol.18 , pp. 495
- Ameer, F.¹ Drewes, S.E.² Freese, S.³ Kaye, P.T.⁴

44
- 84947191160
- (k) Drewes, S. E.; Freese, S. D.; Emslie, N. D.; Roos, G. H. P. Synth. Commun. 1988, 18, 1565.
- (1988) Synth. Commun , vol.18 , pp. 1565
- Drewes, S.E.¹ Freese, S.D.² Emslie, N.D.³ Roos, G.H.P.⁴

45
- 37349096494
- -1.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.