Regioselective synthesis of N-functionalized 12-membered azapyridinomacrocycles bearing trialkylcarboxylic acid side chains

被引：31

作者：

Siaugue, JM

Segat-Dioury, F

Sylvestre, I

Favre-Réguillon, A

Foos, J

Madic, C

Guy, A

机构：

[1] Conservatoire Natl Arts & Metiers, ESA CNRS 7084, Chim Organ Lab, F-75141 Paris 3, France

[2] Conservatoire Natl Arts & Metiers, Nucl Sci Lab, F-75003 Paris, France

[3] CEA, Direct Cycle Combustible, F-91191 Gif Sur Yvette, France

来源：

TETRAHEDRON | 2001年 / 57卷 / 22期

关键词：

aza compounds; macrocycles; protecting groups;

D O I：

10.1016/S0040-4020(01)00328-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Selective protection of primary amine moieties of diethylenetriamine by 2-nitrophenylsulfonyl chloride followed by alkylation of the central N atom generates functionalized disulfonamide building blocks. When reacted with 2,6-bis(bromomethyl)pyridine following the Richman-Atkins methodology, such compounds yield the corresponding pyridine-containing azamacrocycles. Smooth removal of the N-sulfonyl groups provides versatile azamacrocyclic intermediates with transannular secondary amine functions. Subsequent N-alkylation regioselectively leads to tri N-functionalized 12-membered azapyridinomacrocycles bearing a sequence of N-acetate and N-propionate side chains. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4713 / 4718

页数：6

共 27 条

[1] Synthesis and NMR studies of three pyridine-containing triaza macrocyclic triacetate ligands and their complexes with lanthanide ions [J].