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Journal of Organic Chemistry

Volumn 67, Issue 26, 2002, Pages 9414-9416

Cyclic alkenenitriles: Chemoselective oxonitrile cyclizations

(4) Fleming, Fraser F a Funk, Lee A a Altundas, Ramazan a Sharief, Vaqar a

a DUQUESNE UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMOSELECTIVE CYCLIZATIONS; DOMINO DEPROTONATION;

DEHYDRATION; NITRILE RESINS;

OLEFINS;

ALKENENITRILE; ANION; CARBONYL DERIVATIVE; CARBOXYL GROUP; HETEROCYCLIC COMPOUND; NITRILE; OXONITRILE; UNCLASSIFIED DRUG;

ACIDITY; ADDITION REACTION; ARTICLE; CYCLIZATION; DEHYDRATION;

EID: 0037184770 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo026396+ Document Type: Article

Times cited : (24)

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- o-p (a) Fleming, F. F.; Guo, J.; Wang, Q.; Weaver, D. J. Org. Chem. 1999, 64, 8568. (b) Fleming, F. F.; Huang, A. Sharief, V.; Pu, Y. J. Org. Chem. 1999, 64, 2830. (c) Haase-Held, M.; Hatzis, M.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1993, 2907. (d) Haase-Held, M.; Hatzis, M.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1992, 2999. (e) Kulkarni, B. A.; Ganesan, A. Angew. Chem., Int. Ed. 1997, 36, 2454. (f) Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (g) Gorlitzer K. Arch. Pharm. 1975, 308, 700. (h) Ikeda, M.; Uchino, T.; Maruyama, K.; Sato, A. Heterocycles 1988, 27, 2349. (i) Bossio, R.; Marcaccini, S.; Pepino, R.; Torroba, T. Synthesis 1993, 783. (j) Orlemans, E. O. M.; Schreuder, A. H.; Conti, P. G. M.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1987, 43, 3817. (k) Verboom, W.; Orlemans, E. O. M.; Berga, H. J.; Scheltinga, M. W.; Reinhoudt, D. N. Tetrahedron 1986, 42, 5053. (l) Verboom, W.; Berga, H. J.; Trompenaars, W. P.; Reinhoudt, D. N. Tetrahedron Lett. 1985, 685. (m) Stefancich, G.; Artico, M.; Massa, S.; Vomero, S. J. Heterocyclic Chem. 1979, 16, 1443. (n) Flitsch, W.; Lerner, H.; Zimmermann, H. Chem. Ber. 1977, 110, 2765. (o) Nakashima, K.; Inoue, K.; Sono, M.; Tori, M. J. Org. Chem. 2002, 67, 6034. (p) For a similar one-step cyclization see: Elghamry, I.; Dopp, D.; Henkel, G. Synthesis 2001, 1223.
- (1987) Tetrahedron , vol.43 , pp. 3817
- Orlemans, E.O.M.¹ Schreuder, A.H.² Conti, P.G.M.³ Verboom, W.⁴ Reinhoudt, D.N.⁵

31
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- (1986) Tetrahedron , vol.42 , pp. 5053
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32
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- (1985) Tetrahedron Lett. , pp. 685
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33
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- (1979) Heterocyclic Chem. , vol.16 , pp. 1443
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34
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- Flitsch, W.¹ Lerner, H.² Zimmermann, H.³

35
- 0037162784
- o-p (a) Fleming, F. F.; Guo, J.; Wang, Q.; Weaver, D. J. Org. Chem. 1999, 64, 8568. (b) Fleming, F. F.; Huang, A. Sharief, V.; Pu, Y. J. Org. Chem. 1999, 64, 2830. (c) Haase-Held, M.; Hatzis, M.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1993, 2907. (d) Haase-Held, M.; Hatzis, M.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1992, 2999. (e) Kulkarni, B. A.; Ganesan, A. Angew. Chem., Int. Ed. 1997, 36, 2454. (f) Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825. (g) Gorlitzer K. Arch. Pharm. 1975, 308, 700. (h) Ikeda, M.; Uchino, T.; Maruyama, K.; Sato, A. Heterocycles 1988, 27, 2349. (i) Bossio, R.; Marcaccini, S.; Pepino, R.; Torroba, T. Synthesis 1993, 783. (j) Orlemans, E. O. M.; Schreuder, A. H.; Conti, P. G. M.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1987, 43, 3817. (k) Verboom, W.; Orlemans, E. O. M.; Berga, H. J.; Scheltinga, M. W.; Reinhoudt, D. N. Tetrahedron 1986, 42, 5053. (l) Verboom, W.; Berga, H. J.; Trompenaars, W. P.; Reinhoudt, D. N. Tetrahedron Lett. 1985, 685. (m) Stefancich, G.; Artico, M.; Massa, S.; Vomero, S. J. Heterocyclic Chem. 1979, 16, 1443. (n) Flitsch, W.; Lerner, H.; Zimmermann, H. Chem. Ber. 1977, 110, 2765. (o) Nakashima, K.; Inoue, K.; Sono, M.; Tori, M. J. Org. Chem. 2002, 67, 6034. (p) For a similar one-step cyclization see: Elghamry, I.; Dopp, D.; Henkel, G. Synthesis 2001, 1223.
- (2002) J. Org. Chem. , vol.67 , pp. 6034
- Nakashima, K.¹ Inoue, K.² Sono, M.³ Tori, M.⁴

36
- 85087227987
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- (2001) Synthesis , pp. 1223
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37
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48
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51
- 0347151321
- note
- No observable reaction occurs with less than 2 equiv of t-BuOK.

52
- 0032541260
- t-BuOK is estimated to have an acidity comparable to LiHMDS in THF: Hartwig, J. F. Angew. Chem. 1998, 37, 2046. For recent deprotonations of alkanenitriles with t-BuOK see: Bunlaksananusorn, T.; Rodriguez, A. L.; Knochel, P. Chem. Commun. 2001, 745. For the extremely high basicity in DMSO see: Cram, D. J.; Rickborn, B.; Knox, G. R. J. Am. Chem. Soc. 1960, 82, 6412.
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53
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- Bunlaksananusorn, T.¹ Rodriguez, A.L.² Knochel, P.³

54
- 0012183573
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- Cram, D.J.¹ Rickborn, B.² Knox, G.R.³

55
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- Aldol condensation prevents the use of enolizable aldehydes. For an excellent intermolecular addition to aromatic aldehydes see: Kisanga, P. B.; Verkade, J. G. J. Org. Chem. 2002, 67, 426.
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- Kisanga, P.B.¹ Verkade, J.G.²

56
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57
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- Michael, J.P.¹ Jungmann, C.M.²

58
- 0346521008
- note
- Performing the reaction at reflux causes partial nitrile hydrolysis to the corresponding amide.

59
- 0345890126
- note
- Use of excess t-BuOK (5 equiv) causes decyanation to 2-phenylcyclohexadiene:

60
- 84985222576
- A rapid proton transfer is observed with related ester enolate nitriles: Stetter, H.; Marten, K. Liebigs Ann. Chem. 1982, 240.
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61
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62
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63
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64
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- Cyclopentanecarbonitriles seem prone to hydrolysis: Jaroszewski, J. W.; Olafsdottir, E. S.; Cornett, C.; Schaumberg, K. Acta Chem. Scand. 1987, B41, 410.
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65
- 0001608912
- For general experimental procedures see: Fleming, F. F.; Hussain, Z.; Weaver, D.; Norman, R. E. J. Org. Chem. 1997, 62, 1305. The high-resolution mass spectra were recorded at The Ohio State University Campus Chemical Instrumentation Center.
- (1997) J. Org. Chem. , vol.62 , pp. 1305
- Fleming, F.F.¹ Hussain, Z.² Weaver, D.³ Norman, R.E.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.