Concise Synthesis of Tetrazole Macrocycle
Posted on 2017-09-13 - 14:16
A concise two step synthesis of tetrazole
containing macrocycles
from readily accessible starting materials is presented. The first
step comprises a chemoselective amidation of amino acid derived isocyanocarboxylicacid
esters with unprotected symmetrical diamines to afford diverse α-isocyano-ω-amines.
In the second step, the α-isocyano-ω-amines undergo an
Ugi tetrazole reaction to close the macrocycle. Advantageously, this
strategy allows short access to 11–19-membered macrocycles
in which substituents can be independently varied at three different
positions.
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Abdelraheem, Eman M.
M.; de Haan, Michel P.; Patil, Pravin; Kurpiewska, Katarzyna; Kalinowska-Tłuścik, Justyna; Shaabani, Shabnam; et al. (2017). Concise Synthesis of Tetrazole Macrocycle. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b02319
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AUTHORS (7)
EA
Eman M.
M. Abdelraheem
Md
Michel P. de Haan
PP
Pravin Patil
KK
Katarzyna Kurpiewska
JK
Justyna Kalinowska-Tłuścik
SS
Shabnam Shaabani
AD
Alexander Dömling