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

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 24期

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 [J].

BERGERON, RJ ;

MCMANIS, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (09) :1700-1703

[2] Natural guanidine derivatives [J].

Berlinck, RGS .

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 [J].

BERNATOWICZ, MS ;

WU, YL ;

MATSUEDA, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2497-2502

[4] URETHANE PROTECTED DERIVATIVES OF 1-GUANYLPYRAZOLE FOR THE MILD AND EFFICIENT PREPARATION OF GUANIDINES [J].

BERNATOWICZ, MS ;

WU, YL ;

MATSUEDA, GR .

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 [J].

Feichtinger, K ;

Sings, HL ;

Baker, TJ ;

Matthews, K ;

Goodman, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8432-8439

[7] Diprotected triflylguanidines: A new class of guanidinylation reagents [J].

Feichtinger, K ;

Zapf, C ;

Sings, HL ;

Goodman, M .

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 [J].

Guo, ZX ;

Cammidge, AN ;

Horwell, DC .

SYNTHETIC COMMUNICATIONS, 2000, 30 (16) :2933-2943