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Volumn 28, Issue 2, 1998, Pages 261-276

Studies on the transformation of azido-group to N-(t-butoxycarbonyl)amino group via Staudinger reaction

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AZIDE; BICARBONATE; BUTYLATE; CARBONYL DERIVATIVE; PHOSPHINE;

EID: 0031886104     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808005719     Document Type: Article
Times cited : (19)

References (55)
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    • For reviews, see: a) Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353. b) Johnson, A. W.; Kaska, W. C.; Starzewski, K. A. O.; Dixon, D. A. Ylides and Imines of Phosphorus; John Wiley & Sons, Inc; 1993; pp. 435. c) Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757.
    • (1993) Ylides and Imines of Phosphorus , pp. 435
    • Johnson, A.W.1    Kaska, W.C.2    Starzewski, K.A.O.3    Dixon, D.A.4
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    • For reviews, see: a) Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353. b) Johnson, A. W.; Kaska, W. C.; Starzewski, K. A. O.; Dixon, D. A. Ylides and Imines of Phosphorus; John Wiley & Sons, Inc; 1993; pp. 435. c) Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5757
    • Taber, D.F.1    You, K.K.2
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    • Some reported examples of hydrolysis using basic conditions: a) Kappe, Th.; Pfaffenschlager, A.; Stadibauer, W. Synthesis 1989, 666. b) Baum, K.; Berkowitz, P.; Grakauskas, V.; Archibald, T. G. J. Org. Chem. 1983, 48, 2953. c) Mungall, W. S.; Greene, G. L.; Heavner G. A.; Letsinger R. L. J. Org. Chem. 1975, 40, 1659. d) Murashi, S.-I.; Tanigawa, Y.; Imada, Y.; Taniguchi, Y. Tetrahedron Lett. 1986, 27, 227. e) Katritzky, A. R.; Jiang, J.; Urogdi, L. Tetrahedron Lett. 1989, 25, 3303.
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    • Kappe, Th.1    Pfaffenschlager, A.2    Stadibauer, W.3
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    • Some reported examples of hydrolysis using basic conditions: a) Kappe, Th.; Pfaffenschlager, A.; Stadibauer, W. Synthesis 1989, 666. b) Baum, K.; Berkowitz, P.; Grakauskas, V.; Archibald, T. G. J. Org. Chem. 1983, 48, 2953. c) Mungall, W. S.; Greene, G. L.; Heavner G. A.; Letsinger R. L. J. Org. Chem. 1975, 40, 1659. d) Murashi, S.-I.; Tanigawa, Y.; Imada, Y.; Taniguchi, Y. Tetrahedron Lett. 1986, 27, 227. e) Katritzky, A. R.; Jiang, J.; Urogdi, L. Tetrahedron Lett. 1989, 25, 3303.
    • (1983) J. Org. Chem. , vol.48 , pp. 2953
    • Baum, K.1    Berkowitz, P.2    Grakauskas, V.3    Archibald, T.G.4
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    • Some reported examples of hydrolysis using basic conditions: a) Kappe, Th.; Pfaffenschlager, A.; Stadibauer, W. Synthesis 1989, 666. b) Baum, K.; Berkowitz, P.; Grakauskas, V.; Archibald, T. G. J. Org. Chem. 1983, 48, 2953. c) Mungall, W. S.; Greene, G. L.; Heavner G. A.; Letsinger R. L. J. Org. Chem. 1975, 40, 1659. d) Murashi, S.-I.; Tanigawa, Y.; Imada, Y.; Taniguchi, Y. Tetrahedron Lett. 1986, 27, 227. e) Katritzky, A. R.; Jiang, J.; Urogdi, L. Tetrahedron Lett. 1989, 25, 3303.
    • (1975) J. Org. Chem. , vol.40 , pp. 1659
    • Mungall, W.S.1    Greene, G.L.2    Heavner, G.A.3    Letsinger, R.L.4
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    • Some reported examples of hydrolysis using basic conditions: a) Kappe, Th.; Pfaffenschlager, A.; Stadibauer, W. Synthesis 1989, 666. b) Baum, K.; Berkowitz, P.; Grakauskas, V.; Archibald, T. G. J. Org. Chem. 1983, 48, 2953. c) Mungall, W. S.; Greene, G. L.; Heavner G. A.; Letsinger R. L. J. Org. Chem. 1975, 40, 1659. d) Murashi, S.-I.; Tanigawa, Y.; Imada, Y.; Taniguchi, Y. Tetrahedron Lett. 1986, 27, 227. e) Katritzky, A. R.; Jiang, J.; Urogdi, L. Tetrahedron Lett. 1989, 25, 3303.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 227
    • Murashi, S.-I.1    Tanigawa, Y.2    Imada, Y.3    Taniguchi, Y.4
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    • Some reported examples of hydrolysis using basic conditions: a) Kappe, Th.; Pfaffenschlager, A.; Stadibauer, W. Synthesis 1989, 666. b) Baum, K.; Berkowitz, P.; Grakauskas, V.; Archibald, T. G. J. Org. Chem. 1983, 48, 2953. c) Mungall, W. S.; Greene, G. L.; Heavner G. A.; Letsinger R. L. J. Org. Chem. 1975, 40, 1659. d) Murashi, S.-I.; Tanigawa, Y.; Imada, Y.; Taniguchi, Y. Tetrahedron Lett. 1986, 27, 227. e) Katritzky, A. R.; Jiang, J.; Urogdi, L. Tetrahedron Lett. 1989, 25, 3303.
    • (1989) Tetrahedron Lett. , vol.25 , pp. 3303
    • Katritzky, A.R.1    Jiang, J.2    Urogdi, L.3
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    • Some reported examples of hydrolysis using acidic conditions: a) Koziara, A.; Osowska-Pacewicka, K.; Zawadzki, S.; Zwierzak, A. Synthesis 1985, 202. b) Koziara, A.; Zwierzak, A. Tetrahedron Lett. 1987, 28, 6513. c) Hankovszky, H. O.; Hideg, K.; Lex, L. Synthesis 1981, 147. d) Fabiano, E.; Golding, B. T.; Sadeghi, M. M. Synthesis 1987, 190. e) Knouzi, N.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr 1985, 815.
    • (1985) Synthesis , pp. 202
    • Koziara, A.1    Osowska-Pacewicka, K.2    Zawadzki, S.3    Zwierzak, A.4
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    • 0001164135 scopus 로고
    • Some reported examples of hydrolysis using acidic conditions: a) Koziara, A.; Osowska-Pacewicka, K.; Zawadzki, S.; Zwierzak, A. Synthesis 1985, 202. b) Koziara, A.; Zwierzak, A. Tetrahedron Lett. 1987, 28, 6513. c) Hankovszky, H. O.; Hideg, K.; Lex, L. Synthesis 1981, 147. d) Fabiano, E.; Golding, B. T.; Sadeghi, M. M. Synthesis 1987, 190. e) Knouzi, N.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr 1985, 815.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6513
    • Koziara, A.1    Zwierzak, A.2
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    • 85077636641 scopus 로고
    • Some reported examples of hydrolysis using acidic conditions: a) Koziara, A.; Osowska-Pacewicka, K.; Zawadzki, S.; Zwierzak, A. Synthesis 1985, 202. b) Koziara, A.; Zwierzak, A. Tetrahedron Lett. 1987, 28, 6513. c) Hankovszky, H. O.; Hideg, K.; Lex, L. Synthesis 1981, 147. d) Fabiano, E.; Golding, B. T.; Sadeghi, M. M. Synthesis 1987, 190. e) Knouzi, N.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr 1985, 815.
    • (1981) Synthesis , pp. 147
    • Hankovszky, H.O.1    Hideg, K.2    Lex, L.3
  • 19
    • 0002709104 scopus 로고
    • Some reported examples of hydrolysis using acidic conditions: a) Koziara, A.; Osowska-Pacewicka, K.; Zawadzki, S.; Zwierzak, A. Synthesis 1985, 202. b) Koziara, A.; Zwierzak, A. Tetrahedron Lett. 1987, 28, 6513. c) Hankovszky, H. O.; Hideg, K.; Lex, L. Synthesis 1981, 147. d) Fabiano, E.; Golding, B. T.; Sadeghi, M. M. Synthesis 1987, 190. e) Knouzi, N.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr 1985, 815.
    • (1987) Synthesis , pp. 190
    • Fabiano, E.1    Golding, B.T.2    Sadeghi, M.M.3
  • 20
    • 0001073140 scopus 로고
    • Some reported examples of hydrolysis using acidic conditions: a) Koziara, A.; Osowska-Pacewicka, K.; Zawadzki, S.; Zwierzak, A. Synthesis 1985, 202. b) Koziara, A.; Zwierzak, A. Tetrahedron Lett. 1987, 28, 6513. c) Hankovszky, H. O.; Hideg, K.; Lex, L. Synthesis 1981, 147. d) Fabiano, E.; Golding, B. T.; Sadeghi, M. M. Synthesis 1987, 190. e) Knouzi, N.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr 1985, 815.
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    • Knouzi, N.1    Vaultier, M.2    Carrié, R.3
  • 22
    • 85036675299 scopus 로고    scopus 로고
    • 3 work-up, the product 2h was isolated in the same overall yield
    • 3 work-up, the product 2h was isolated in the same overall yield.
  • 23
    • 85036676684 scopus 로고    scopus 로고
    • 1H NMR
    • 1H NMR.
  • 25
    • 85036681969 scopus 로고    scopus 로고
    • 3 (1 eq) where used, only traces of 2h and 2b were detected by TLC
    • 3 (1 eq) where used, only traces of 2h and 2b were detected by TLC.
  • 26
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    • An authentic sample of 6 was prepared from monoazide 5 using known methodology for the synthesis of symmetrical ureas: Izdebski, J.; Pawlak, D. Synthesis 1989, 423.
    • (1989) Synthesis , pp. 423
    • Izdebski, J.1    Pawlak, D.2
  • 27
    • 85036677357 scopus 로고    scopus 로고
    • The formation of more polar compounds was observed but they were unsuccessfully isolated because of extensive contamination with tri-n-butylphosphine oxide
    • The formation of more polar compounds was observed but they were unsuccessfully isolated because of extensive contamination with tri-n-butylphosphine oxide.
  • 30
    • 0040935404 scopus 로고    scopus 로고
    • 2/DMAP has been recently studied: Knölker, H.-J.; Braxmeier, T.; Schlectingen, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 2497; Knölker, H.-J.; Braxmeier, T.; Schlectingen, G. Synlett 1996, 502.
    • (1996) Synlett , pp. 502
    • Knölker, H.-J.1    Braxmeier, T.2    Schlectingen, G.3
  • 35
    • 0025915036 scopus 로고
    • Alkyl isocyanates are known to react slowly at room temperature with tertiary alcohols to give the corresponding carbamates: Benalil, A.; Roby, P.; Carboni, B.; Vaultier, M. Synthesis 1991, 787..
    • (1991) Synthesis , pp. 787
    • Benalil, A.1    Roby, P.2    Carboni, B.3    Vaultier, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.