Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

被引：9

作者：

Zhang, Xiaofeng ^{[1
,2
,3
]}

Ma, Xiaoming ^{[4
]}

Zhang, Wei ^{[1
,2
]}

机构：

[1] Univ Massachusetts Boston, Ctr Green Chem, 100 Morrissey Blvd, Boston, MA 02125 USA

[2] Univ Massachusetts Boston, Dept Chem, 100 Morrissey Blvd, Boston, MA 02125 USA

[3] Cerevel Therapeut, Dept Med Chem, 222 Jacobs St Suite 200, Cambridge, MA 02141 USA

[4] Changzhou Univ, Sch Pharm, Changzhou 213164, Peoples R China

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 19卷

关键词：

3+2] cycloaddition; decarboxylation; 1,3-dipolar; double cycloaddition; one-pot synthesis; multicomponent reaction; semi-stabilized azomethine ylide; NONSTABILIZED AZOMETHINE YLIDES; DIVERSITY-ORIENTED SYNTHESIS; ONE-POT; 2-AZAALLYL ANIONS; ORGANIC-SYNTHESIS; PYRROLIDINES; INHIBITORS; FULLERENE; SYSTEMS; ROUTE;

D O I：

10.3762/bjoc.19.123

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The [3 + 2] cycloadditions of stabilized azomethine ylides (AMYs) derived from amino esters are well-established. However, the reactions of semi-stabilized AMYs generated from decarboxylative condensation of alpha-amino acids with arylaldehydes are much less explored. The [3 + 2] adducts of alpha-amino acids could be used for a second [3 + 2] cycloaddition as well as for other post-con-densation modifications. This article highlights our recent work on the development of alpha-amino acid-based [3 + 2] cycloaddition reactions of N-H-type AMYs in multicomponent, one-pot, and stepwise reactions for the synthesis of diverse heterocycles related to some bioactive compounds and natural products.

引用

页码：1677 / 1693

页数：17

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