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Volumn 64, Issue 23, 1999, Pages 8702-8705

Effective preparation of O-succinimidyl-2(tert- butoxycarbonylamino)ethylcarbamate derivatives from β-amino acids. Application to the synthesis of urea-containing pseudopeptides and oligoureas

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; PSEUDOPEPTIDE; SUCCINIMIDE DERIVATIVE; UREA DERIVATIVE;

EID: 0033550306     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990092e     Document Type: Article
Times cited : (78)

References (30)
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    • For use of phosgene and its derivatives, see: (a) Majer, P.; Randad, R. S. J. Org. Chem. 1994, 59, 1937. (b) Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. J. Org. Chem. 1998, 63, 4802-4807. For use of various carbonates, see: (c) Takeda, K.; Akagi, Y.; Saiki, A.; Tsukahara, T.; Ogura, H. Tetrahedron Lett. 1983, 24, 4569. Izdebski, J.; Pawlak, D. Synthesis 1989, 423. For use of N,N′- carbonyldiimidazole, see: (d) Zhang, X.; Rodrigues, J.; Evans, L.; Hinckle, B.; Ballantyne, L.; Pena, M. J. Org. Chem. 1997, 62, 6420.
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    • For use of phosgene and its derivatives, see: (a) Majer, P.; Randad, R. S. J. Org. Chem. 1994, 59, 1937. (b) Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. J. Org. Chem. 1998, 63, 4802-4807. For use of various carbonates, see: (c) Takeda, K.; Akagi, Y.; Saiki, A.; Tsukahara, T.; Ogura, H. Tetrahedron Lett. 1983, 24, 4569. Izdebski, J.; Pawlak, D. Synthesis 1989, 423. For use of N,N′- carbonyldiimidazole, see: (d) Zhang, X.; Rodrigues, J.; Evans, L.; Hinckle, B.; Ballantyne, L.; Pena, M. J. Org. Chem. 1997, 62, 6420.
    • (1998) J. Org. Chem. , vol.63 , pp. 4802-4807
    • Scialdone, M.A.1    Shuey, S.W.2    Soper, P.3    Hamuro, Y.4    Burns, D.M.5
  • 16
    • 49049127243 scopus 로고
    • For use of phosgene and its derivatives, see: (a) Majer, P.; Randad, R. S. J. Org. Chem. 1994, 59, 1937. (b) Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. J. Org. Chem. 1998, 63, 4802-4807. For use of various carbonates, see: (c) Takeda, K.; Akagi, Y.; Saiki, A.; Tsukahara, T.; Ogura, H. Tetrahedron Lett. 1983, 24, 4569. Izdebski, J.; Pawlak, D. Synthesis 1989, 423. For use of N,N′- carbonyldiimidazole, see: (d) Zhang, X.; Rodrigues, J.; Evans, L.; Hinckle, B.; Ballantyne, L.; Pena, M. J. Org. Chem. 1997, 62, 6420.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 4569
    • Takeda, K.1    Akagi, Y.2    Saiki, A.3    Tsukahara, T.4    Ogura, H.5
  • 17
    • 85082702911 scopus 로고
    • For use of phosgene and its derivatives, see: (a) Majer, P.; Randad, R. S. J. Org. Chem. 1994, 59, 1937. (b) Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. J. Org. Chem. 1998, 63, 4802-4807. For use of various carbonates, see: (c) Takeda, K.; Akagi, Y.; Saiki, A.; Tsukahara, T.; Ogura, H. Tetrahedron Lett. 1983, 24, 4569. Izdebski, J.; Pawlak, D. Synthesis 1989, 423. For use of N,N′- carbonyldiimidazole, see: (d) Zhang, X.; Rodrigues, J.; Evans, L.; Hinckle, B.; Ballantyne, L.; Pena, M. J. Org. Chem. 1997, 62, 6420.
    • (1989) Synthesis , pp. 423
    • Izdebski, J.1    Pawlak, D.2
  • 18
    • 0000747972 scopus 로고    scopus 로고
    • For use of phosgene and its derivatives, see: (a) Majer, P.; Randad, R. S. J. Org. Chem. 1994, 59, 1937. (b) Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. J. Org. Chem. 1998, 63, 4802-4807. For use of various carbonates, see: (c) Takeda, K.; Akagi, Y.; Saiki, A.; Tsukahara, T.; Ogura, H. Tetrahedron Lett. 1983, 24, 4569. Izdebski, J.; Pawlak, D. Synthesis 1989, 423. For use of N,N′-carbonyldiimidazole, see: (d) Zhang, X.; Rodrigues, J.; Evans, L.; Hinckle, B.; Ballantyne, L.; Pena, M. J. Org. Chem. 1997, 62, 6420.
    • (1997) J. Org. Chem. , vol.62 , pp. 6420
    • Zhang, X.1    Rodrigues, J.2    Evans, L.3    Hinckle, B.4    Ballantyne, L.5    Pena, M.6
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    • (b) Reference 3b
    • (b) Reference 3b.
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    • 1,3-Dihydro-2H-benzimidazol-2-ones and related compounds represent attractive families of building blocks having interesting biochemical and pharmacological properties. Regioselective alkylation of 1,3-dihydro-2H-benzimidazol-2-one and structurally related cyclic urea analogues was reported by Meanwell et al. through the use of monoalkoxycarbonyl derivatives (including compound 5). In this paper, 5 was synthesized by treatment of 1,3-dihydrobenzimidazol-2-one with NaH followed by an excess of di-tert-butyl dicarbonate. Meanwell, N. A.; Sit, S. Y.; Gao, J.; Wong, H. S.; Gao, Q.; St Laurent, D. R.; Balasubramanian, N. J. Org. Chem. 1995, 60, 1565.
    • (1995) J. Org. Chem. , vol.60 , pp. 1565
    • Meanwell, N.A.1    Sit, S.Y.2    Gao, J.3    Wong, H.S.4    Gao, Q.5    St Laurent, D.R.6    Balasubramanian, N.7
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    • It is noteworthy that for the synthesis of oligoanthranilamides the group of Hamilton used 2-nitrobenzoic acid in place of N-benzoylanthranilic acid. In this case, the nitro group as a masked form of the amine was required to avoid the formation of azlactone: Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1996, 118, 7529.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7529
    • Hamuro, Y.1    Geib, S.J.2    Hamilton, A.D.3
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    • note
    • 3-i-Pr (9).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.