SCOPUS 정보 검색 플랫폼

Letters in Organic Chemistry

Volumn 2, Issue 3, 2005, Pages 280-282

Synthesis of β-ketonitriles from 3-bromoisoxazoles

(3) Kociolek, Martin G a Straub, Nicholas G a Marton, Elizabeth J a

a BEHREND COLLEGE (United States)

Author keywords

Ferrous chloride; Isoxazole; Ketonitrile; Molybdenum hexacarbonyl; Reductive ring opening

Indexed keywords

EID: 43449123915 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/1570178053765302 Document Type: Review

Times cited : (10)

References (49)

1
- 0000562763
- (a) McGregor, D. N.; Corbin, U.; Swigor, J. E.; Cheney, L. C. Tetrahedron 1969, 25, 389-395;
- (1969) Tetrahedron , vol.25 , pp. 389-395
- McGregor, D.N.¹ Corbin, U.² Swigor, J.E.³ Cheney, L.C.⁴

2
- 0344674225
- (b) Auricchio, S.; Ricca, A.; Vajna De Pava, O. Gazz. Chim. Ital. 1980, 110, 567-569;
- (1980) Gazz. Chim. Ital , vol.110 , pp. 567-569
- Auricchio, S.¹ Ricca, A.² Vajna De Pava, O.³

3
- 0018907078
- (c) Auricchio, S.; Ricca, A.; Vajna De Pava, O. Tetrahedron Lett. 1980, 21, 857-858;
- (1980) Tetrahedron Lett , vol.21 , pp. 857-858
- Auricchio, S.¹ Ricca, A.² Vajna De Pava, O.³

4
- 0003607021
- Katrizky, A. R, Rees, C. W. Eds, Pergamon Press: Oxford
- (d) Kozikowski, A. P. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R.; Rees, C. W. Eds.; Pergamon Press: Oxford, 1984; Vol. 1; pp. 453-476;
- (1984) Comprehensive Heterocyclic Chemistry , vol.1 , pp. 453-476
- Kozikowski, A.P.¹

5
- 0012444107
- (e) Baraldi, P. G.; Barco, A.; Benetti, S.; Manfredini, S.; Pollini, G. P.; Simoni, D. Tetrahedron Lett. 1984, 25, 4313-4316;
- (1984) Tetrahedron Lett , vol.25 , pp. 4313-4316
- Baraldi, P.G.¹ Barco, A.² Benetti, S.³ Manfredini, S.⁴ Pollini, G.P.⁵ Simoni, D.⁶

6
- 0023618387
- (f) Baraldi, P. G.; Barco, A.; Benetti, S.; Pollini, G. P.; Simoni, D. Synthesis 1987, 857-869;
- (1987) Synthesis , pp. 857-869
- Baraldi, P.G.¹ Barco, A.² Benetti, S.³ Pollini, G.P.⁴ Simoni, D.⁵

7
- 0004027441
- Interscie-nce: New York
- (g) Grunanger, P.; Vita Finzi, P. Isoxazoles; Interscie-nce: New York, 1991;
- (1991) Isoxazoles
- Grunanger, P.¹ Vita Finzi, P.²

8
- 0000142011
- (h) Dawood, K. M.; Kandeel, Z. E.; Farag, A. M. Heteroat. Chem. 1999, 10, 417-422;
- (1999) Heteroat. Chem , vol.10 , pp. 417-422
- Dawood, K.M.¹ Kandeel, Z.E.² Farag, A.M.³

9
- 0037029795
- (i) Li, C.-S.; Lacasse, E. Tetrahedron Lett. 2002, 43, 3565-3568.
- (2002) Tetrahedron Lett , vol.43 , pp. 3565-3568
- Li, C.-S.¹ Lacasse, E.²

10
- 46249093470
- (a) Dela Cal, M. T.; Cristobal, B. I.; Cuadrado, P.; Gonzalez, A. M.; Pulido, F. J. Synth. Commun. 1989, 19, 1039-1045;
- (1989) Synth. Commun , vol.19 , pp. 1039-1045
- Dela Cal, M.T.¹ Cristobal, B.I.² Cuadrado, P.³ Gonzalez, A.M.⁴ Pulido, F.J.⁵

11
- 0028903264
- (b) Gonzalez, B.; Gonzalez, A. M.; Pulido, F. J. Synth. Commun. 1995, 25, 1005-1014;
- (1995) Synth. Commun , vol.25 , pp. 1005-1014
- Gonzalez, B.¹ Gonzalez, A.M.² Pulido, F.J.³

12
- 0034733522
- (c) Fuentes, J. A.; Maestro, A.; Testera, A. M.; Banez, J. M. Tetrahedron: Asymmetry 2000, 1, 2565-2577.
- (2000) Tetrahedron: Asymmetry , vol.1 , pp. 2565-2577
- Fuentes, J.A.¹ Maestro, A.² Testera, A.M.³ Banez, J.M.⁴

13
- 37049096266
- (a) Nitta, M.; Kobayashi, T. J. Chem. Soc. Chem. Comm. 1982, 877-878;
- (1982) J. Chem. Soc. Chem. Comm , pp. 877-878
- Nitta, M.¹ Kobayashi, T.²

14
- 46249087666
- (b) Kobayashi, T.; Nitta, M. Chem. Lett. 1983, 1233-1236;
- (1983) Chem. Lett , pp. 1233-1236
- Kobayashi, T.¹ Nitta, M.²

15
- 3142711194
- (c) Kobayashi, T.; Nitta, M. Bull. Chem. Soc. Jpn. 1985, 58, 152-157;
- (1985) Bull. Chem. Soc. Jpn , vol.58 , pp. 152-157
- Kobayashi, T.¹ Nitta, M.²

16
- 0001416457
- (d) Niita, M.; Yi, A.; Kobayashi, T. Bull. Chem. Soc. Jpn. 1985, 58, 991-994;
- (1985) Bull. Chem. Soc. Jpn , vol.58 , pp. 991-994
- Niita, M.¹ Yi, A.² Kobayashi, T.³

17
- 1042308183
- (e) Nitta, M.; Kobayashi, T. J. Chem. Soc. Perkin Trans. J 1985, 1401-1406;
- (1985) J. Chem. Soc. Perkin Trans. J , pp. 1401-1406
- Nitta, M.¹ Kobayashi, T.²

18
- 84986433392
- (f) Baraldi, P. G.; Barco, A.; Benetti, S.; Manfredini, S.; Simoni, D. Synthesis 1987, 276-278;
- (1987) Synthesis , pp. 276-278
- Baraldi, P.G.¹ Barco, A.² Benetti, S.³ Manfredini, S.⁴ Simoni, D.⁵

19
- 0000014677
- (g) Nitta, M.; Higuchi, T. Heterocycles 1994, 38, 853-857;
- (1994) Heterocycles , vol.38 , pp. 853-857
- Nitta, M.¹ Higuchi, T.²

20
- 0006055130
- (h) Anderson-McKay, J.; Savage, G. P.; Simpson, G. W. Aust. J. Chem. 1996, 49, 163-6;
- (1996) Aust. J. Chem , vol.49 , pp. 163-166
- Anderson-McKay, J.¹ Savage, G.P.² Simpson, G.W.³

21
- 0037029795
- (i) Li, C.-S.; Lacasse, E. Tetrahedron Lett. 2002, 43, 3565-3568.
- (2002) Tetrahedron Lett , vol.43 , pp. 3565-3568
- Li, C.-S.¹ Lacasse, E.²

22
- 0000624901
- (a) Natale, N. R. Tetrahedron Lett. 1982, 23, 5009-1502;
- (1982) Tetrahedron Lett , vol.23 , pp. 5009-1502
- Natale, N.R.¹

23
- 0037163293
- (b) Fan, X.; Zhang, Y. Tetrahedron Lett. 2002; 43, 7001-7003.
- (2002) Tetrahedron Lett , vol.43 , pp. 7001-7003
- Fan, X.¹ Zhang, Y.²

24
- 0001475529
- (a) Nitta, M.; Kobayashi, T. Tetrahedron Lett. 1982, 23, 3925-3928;
- (1982) Tetrahedron Lett , vol.23 , pp. 3925-3928
- Nitta, M.¹ Kobayashi, T.²

25
- 0006482133
- (b) Kijima, M.; Nambu, Y.; Endo, T. J. Org. Chem. 1985, 50, 1140-1142;
- (1985) J. Org. Chem , vol.50 , pp. 1140-1142
- Kijima, M.¹ Nambu, Y.² Endo, T.³

26
- 0030791892
- (c) Auricchio, S.; Bini, A.; Pastormerlo, E.; Truscello, A. M. Tetrahedron 1997, 53, 10911-10920.
- (1997) Tetrahedron , vol.53 , pp. 10911-10920
- Auricchio, S.¹ Bini, A.² Pastormerlo, E.³ Truscello, A.M.⁴

27
- 0005955779
- General methods and aliphatic nitriles
- (a) North, M. Nitriles: General methods and aliphatic nitriles. In Comprehensive Organic Functional Group Transformations, 1995; Vol. 3; pp. 611-40, 733-856;
- (1995) Comprehensive Organic Functional Group Transformations , vol.3
- North, M.N.¹

28
- 0038120226
- (b) Hauser, C. R.; Murray, J. G. J. Am. Chem. Soc. 1955, 77, 2851-2852;
- (1955) J. Am. Chem. Soc , vol.77 , pp. 2851-2852
- Hauser, C.R.¹ Murray, J.G.²

29
- 0038120225
- (c) Hauser, C. R.; Eby, C. J. J. Am. Chem. Soc. 1957, 79, 728-731;
- (1957) J. Am. Chem. Soc , vol.79 , pp. 728-731
- Hauser, C.R.¹ Eby, C.J.²

30
- 84981871817
- (d) Baker, B. R.; Jordaan, J. H. J. Heterocycl. Chem. 1966, 3, 324-327;
- (1966) J. Heterocycl. Chem , vol.3 , pp. 324-327
- Baker, B.R.¹ Jordaan, J.H.²

31
- 84986477797
- (e) Augustin, M.; Jahreis, G.; Rudorf, W. D. Synthesis 1977, 472-474;
- (1977) Synthesis , pp. 472-474
- Augustin, M.¹ Jahreis, G.² Rudorf, W.D.³

32
- 84986506885
- (f) Kambe, S.; Saito, K.; Kishi, H.; Sakurai, A.; Midorikawa, H. Synthesis 1979, 287-289;
- (1979) Synthesis , pp. 287-289
- Kambe, S.¹ Saito, K.² Kishi, H.³ Sakurai, A.⁴ Midorikawa, H.⁵

33
- 0028268519
- (g) Koenig, T. M.; Mitchell, D. Tetrahedron Lett. 1994, 35, 1339-1342;
- (1994) Tetrahedron Lett , vol.35 , pp. 1339-1342
- Koenig, T.M.¹ Mitchell, D.²

34
- 0029082232
- (h) Mehmandoust, M.; Buisson, D.; Azerad, R. Tetrahedron Lett. 1995, 36, 6461-6462;
- (1995) Tetrahedron Lett , vol.36 , pp. 6461-6462
- Mehmandoust, M.¹ Buisson, D.² Azerad, R.³

35
- 0030733375
- (i)Watson, S. P.; Wilson, R. D.; Judd, D. B.; Richards, S. A. Tetrahedron Lett. 1997, 38, 9065-9068;
- (1997) Tetrahedron Lett , vol.38 , pp. 9065-9068
- Watson, S.P.¹ Wilson, R.D.² Judd, D.B.³ Richards, S.A.⁴

36
- 0034703151
- (j) Dehli, J. R.; Gotor, V. Tetrahedron: Asymmetry 2000, 11, 3693-3700;
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 3693-3700
- Dehli, J.R.¹ Gotor, V.²

37
- 0000191020
- (k) Dehli, J. R.; Gotor, V. Tetrahedron: Asymmetry 2001, 12, 1485-1492.
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 1485-1492
- Dehli, J.R.¹ Gotor, V.²

38
- 46249125407
- 4) and evaporated. The residue was purified by column chromatography (silica gel; hexanes/ethyl acetate) to give the pure isoxazoles.
- 4) and evaporated. The residue was purified by column chromatography (silica gel; hexanes/ethyl acetate) to give the pure isoxazoles.

39
- 0026715948
- Rohloff J. C.; Robinson, J., III; Gardner, J. O. Tetrahedron Lett. 1992, 33, 3113-3116.
- (1992) Tetrahedron Lett , vol.33 , pp. 3113-3116
- Rohloff, J.C.¹ Robinson III, J.² Gardner, J.O.³

40
- 0023278502
- Chiarino, D.; Napoletano, M.; Sala, A. J. Heterocycl. Chem. 1987, 24, 43-46.
- (1987) J. Heterocycl. Chem , vol.24 , pp. 43-46
- Chiarino, D.¹ Napoletano, M.² Sala, A.³

41
- 46249100491
- 3, 400 MHz)
- 2O: C, 39.10; H, 3.28; N, 13.03; found: C, 39.09; H, 3.16; N, 12.89.

42
- 84986500358
- commercially available from Aldrich; (b) Hackler, R. E.; Burow, K. W. Jr.; Kaster, S. V.; Wickiser, D. I. J. Heterocycl. Chem. 1989, 26, 1575-1578.;
- (a) commercially available from Aldrich; (b) Hackler, R. E.; Burow, K. W. Jr.; Kaster, S. V.; Wickiser, D. I. J. Heterocycl. Chem. 1989, 26, 1575-1578.;

43
- 84970596203
- McFadden, H. G.; Huppatz, J. L. Aust. J. Chem. 1991, 44, 1263-1273;
- (1991) Aust. J. Chem , vol.44 , pp. 1263-1273
- McFadden, H.G.¹ Huppatz, J.L.²

44
- 0002975559
- Hebri, H.; Dunach, E.; Perichon, J. Synlett 1992, 293-294;
- (1992) Synlett , pp. 293-294
- Hebri, H.¹ Dunach, E.² Perichon, J.³

45
- 84885738128
- (c) Effenberger, F.; Null, V. Liebigs Ann. Chem. 1992, 1211-1212;
- (1992) Liebigs Ann. Chem , pp. 1211-1212
- Effenberger, F.¹ Null, V.²

46
- 0026785918
- Effenberger, F.; Null, V.; Ziegler, T. Tetrahedron Lett. 1992, 33, 5157-60;
- (1992) Tetrahedron Lett , vol.33 , pp. 5157-5160
- Effenberger, F.¹ Null, V.² Ziegler, T.³

47
- 84982448928
- (d) Foehlisch, B.; Herter, R.; Wolf, E.; Stezowski, J. J.; Eckle, E. Chem. Ber. 1982, 115, 355-80;
- (1982) Chem. Ber , vol.115 , pp. 355-380
- Foehlisch, B.¹ Herter, R.² Wolf, E.³ Stezowski, J.J.⁴ Eckle, E.⁵

48
- 0035648293
- (e) Gao, Y.; Wang, H.; Xu, M.; Lian, H.; Pan, Y.; Shi, Y. Org. Prep. Proced. Int. 2001, 33, 351-356.
- (2001) Org. Prep. Proced. Int , vol.33 , pp. 351-356
- Gao, Y.¹ Wang, H.² Xu, M.³ Lian, H.⁴ Pan, Y.⁵ Shi, Y.⁶

49
- 46249095329
- Compound 2c: 1H NMR (CDCl3, 400 MHz) 4.75 (s, 2 H, 3.59 (s, 2H, 2.16 (s, 3H, IR (NaCl) 2231, 1734, 1653 cm-1; Anal. Calcd for C6H7 NO3:C, 51.06; H, 5.00; N, 9.93; found: C, 50.92; H, 4.89; N, 9.90. Compound 2g: 1H NMR (CDCl3, 400 MHz) 3.58 (s, 2H, 3.02 (t, J, 6.9 Hz, 2H, 2.64 (t, J, 6.9 Hz, 2H, IR (NaCl) 2252, 1733 cm-1; Anal. Calcd for C6H6N2O:C, 59.01; H, 4.95; N, 22.94; found: C, 58.89; H, 4.86; N, 22.79. Compound 2h: 1H NMR (CDCl3, 400 MHz) 3.51 (s, 2H, 2.82 (t, J, 6.9 Hz, 2H, 2.46 (t, J, 7.0 Hz, 2H, 1.99 (m, 2H, IR (NaCl) 2249, 1732 cm-1; Anal. Calcd for C7HgN2O:C, 61.75; H, 5,92; N, 20.58; found: C, 60.89; H, 5.86; N, 20.47
- 2O:C, 61.75; H, 5,92; N, 20.58; found: C, 60.89; H, 5.86; N, 20.47.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.