Synthesis of pharmacophores containing a prolinate core using a multicomponent 1,3-dipolar cycloaddition of azomethine ylides

被引：7

作者：

Selva, Elisabet ^{[1
,2
,3
,4
]}

Castello, Luis M. ^{[4
]}

Mancebo-Aracil, Juan ^{[5
]}

Selva, Veronica ^{[1
,2
,3
]}

Najera, Carmen ^{[1
,2
]}

Foubelo, Francisco ^{[1
,2
,3
]}

Sansano, Jose M. ^{[1
,2
,3
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

[2] Univ Alicante, Fac Ciencias, Ctr Innovac Quim Avanzada ORFEO CINQA, E-03080 Alicante, Spain

[3] Univ Alicante, Fac Ciencias, Inst Sintesis Organ, E-03080 Alicante, Spain

[4] Medalchemy SL, Ave Ancha de Castelar,46-EA, Alicante 03690, Spain

[5] UNS, Dept Quim, RA-8000 Bahia Blanca, Buenos Aires, Argentina

来源：

TETRAHEDRON | 2017年 / 73卷 / 49期

关键词：

Prolinates; Cycloaddition; Azomethine ylides; Multicomponent; Azanucleoside; C-NUCLEOSIDES; DIVERSITY; ETHYL;

D O I：

10.1016/j.tet.2017.10.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A multicomponent 1,3-dipolar cycloaddition between heterocyclic aldehydes, amino esters and dipolarophiles is efficiently promoted by silver acetate as catalyst, and depending on the nature of the heterocycle and its reactivity the reaction requires 70 degrees C or it to complete. Selected pharmacophores anchored to a formyl group are chromone, 5-methoxyindole, pyridoxal surrogates and a very attractive uracyl derivative. The preference of each tested amino esters towards different dipolarophiles is discussed. At the end, a selective reduction of the ester group allows to obtain a very interesting dideoxiazanucleoside derivative. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：6840 / 6846

页数：7

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