N,N′-Di-tert-butoxycarbonyl-1H-benzotriazole-1-carboxamidine derivatives are highly reactive guanidinylating reagents

被引:48
作者
Musiol, HJ [1 ]
Moroder, L [1 ]
机构
[1] Max Planck Inst Biochem, D-82152 Martinsried, Germany
关键词
D O I
10.1021/ol010191q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] By enhancing the leaving group character of benzotriazole via electron-withdrawing substituents such as the 5-chloro or 6-nitro derivatives with the related N,N'-di-tert butoxycarbonyl-1H-benzotriazole-1-carboxamidines, highly efficient reagents are obtained for conversion of primary and secondary amines in solution and in solid phase to diprotected guanidines.
引用
收藏
页码:3859 / 3861
页数:3
相关论文
共 24 条
  • [1] TOTAL SYNTHESIS OF (+/-)-15-DEOXYSPERGUALIN
    BERGERON, RJ
    MCMANIS, JS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (09) : 1700 - 1703
  • [2] Natural guanidine derivatives
    Berlinck, RGS
    [J]. NATURAL PRODUCT REPORTS, 1999, 16 (03) : 339 - 365
  • [3] 1H-PYRAZOLE-1-CARBOXAMIDINE HYDROCHLORIDE - AN ATTRACTIVE REAGENT FOR GUANYLATION OF AMINES AND ITS APPLICATION TO PEPTIDE-SYNTHESIS
    BERNATOWICZ, MS
    WU, YL
    MATSUEDA, GR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) : 2497 - 2502
  • [4] URETHANE PROTECTED DERIVATIVES OF 1-GUANYLPYRAZOLE FOR THE MILD AND EFFICIENT PREPARATION OF GUANIDINES
    BERNATOWICZ, MS
    WU, YL
    MATSUEDA, GR
    [J]. TETRAHEDRON LETTERS, 1993, 34 (21) : 3389 - 3392
  • [5] DRAKE B, 1994, SYNTHESIS-STUTTGART, P579
  • [6] Triurethane-protected guanidines and triflyldiurethane-protected guanidines: New reagents for guanidinylation reactions
    Feichtinger, K
    Sings, HL
    Baker, TJ
    Matthews, K
    Goodman, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) : 8432 - 8439
  • [7] Diprotected triflylguanidines: A new class of guanidinylation reagents
    Feichtinger, K
    Zapf, C
    Sings, HL
    Goodman, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) : 3804 - 3805
  • [8] Gomes de Souza Berlinck R, 1995, Fortschr Chem Org Naturst, V66, P119
  • [9] Greenhill J V, 1993, Prog Med Chem, V30, P203, DOI 10.1016/S0079-6468(08)70378-3
  • [10] A convenient and versatile method for the synthesis of protected guanidines
    Guo, ZX
    Cammidge, AN
    Horwell, DC
    [J]. SYNTHETIC COMMUNICATIONS, 2000, 30 (16) : 2933 - 2943