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

被引：19

作者：

Afonso, CAM ^{[1
]}

机构：

[1] Univ Nova Lisboa, Fac Ciencias & Tecnol, Dept Quim, P-2825 Monte De Caparica, Portugal

来源：

SYNTHETIC COMMUNICATIONS | 1998年 / 28卷 / 02期

关键词：

D O I：

10.1080/00397919808005719

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By a simple and direct sequence, treatment of primary azides with tri-n-butylphosphine, followed by addition of di-t-butyl dicarbonate (Boc(2)O) affords, N-(t-Butoxycarbonyl)amines 2 in moderate to good overall yields. For secondary azides the formation of symmetrical disubstituted ureas is a competitive process. Conditions were found which, in the presence of a primary amine, allow for moderate selectivity for the reaction with Boc(2)O.

引用

页码：261 / 276

页数：16

共 49 条

[1] TRANSFORMATION OF AZIDO-GROUP TO N-(T-BUTOXYCARBONYL)AMINO GROUP UNDER MILD CONDITIONS VIA STAUDINGER REACTION
AFONSO, CAM
[J]. TETRAHEDRON LETTERS, 1995, 36 (48) : 8857 - 8858
[2] AFONSO CM, 1994, TETRAHEDRON, V50, P9671
[3] Alvarez SG, 1997, SYNTHESIS-STUTTGART, P413
[4] THE FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .26. IONIC SUBSTITUTION-REACTIONS IN GOAGG(IV) CHEMISTRY - THE CONSTRUCTION OF C-N, C-S AND C-C BONDS
BARTON, DHR
CHAVASIRI, W
[J]. TETRAHEDRON, 1994, 50 (01) : 47 - 60
[5] SYNTHESIS OF ELECTRON-DEFICIENT OXETANES - 3-AZIDOOXETANE, 3-NITROOXETANE, AND 3,3-DINITROOXETANE
BAUM, K
BERKOWITZ, PT
GRAKAUSKAS, V
ARCHIBALD, TG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (18) : 2953 - 2956
[6] BENALIL A, 1991, SYNTHESIS-STUTTGART, P787
[7] On the reaction of acyl chlorides and carboxylic anhydrides with phosphazenes
Bosch, I
Gonzalez, A
Urpi, F
Vilarrasa, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) : 5638 - 5643
[8] FABIANO E, 1987, SYNTHESIS-STUTTGART, P190
[9] RECENT ADVANCES IN THE STAUDINGER REACTION
GOLOLOBOV, YG
KASUKHIN, LF
[J]. TETRAHEDRON, 1992, 48 (08) : 1353 - 1406
[10] GREENE TW, 1991, PROTECTIVE GROUPS OR

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