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在深共熔溶剂中通过苯甲酰叠氮化物实现功能化嘧啶和咪唑的区域发散性合成。

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents.

作者信息

Vitale Paola, Cicco Luciana, Cellamare Ilaria, Perna Filippo M, Salomone Antonio, Capriati Vito

机构信息

Dipartimento di Farmacia-Scienze del Farmaco, Università di Bari "Aldo Moro", Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, Italy.

Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali, Università del Salento, Prov.le Lecce-Monteroni, 73100 Lecce, Italy.

出版信息

Beilstein J Org Chem. 2020 Aug 5;16:1915-1923. doi: 10.3762/bjoc.16.158. eCollection 2020.

DOI:10.3762/bjoc.16.158
PMID:32802208
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7418094/
Abstract

We report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32-98% yield) and pyrimidine derivatives (45-88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/urea (1:2 mol/mol)] as environmentally benign and non-innocent reaction media, by modulating the temperature (25 or 80 °C) in the presence or absence of bases (EtN).

摘要

我们报道，当使用深共熔溶剂[氯化胆碱（ChCl）/甘油（1:2摩尔/摩尔）和ChCl/尿素（1:2摩尔/摩尔）]作为环境友好且非惰性的反应介质时，通过在有或没有碱（EtN）存在的情况下调节温度（25或80°C），苯甲酰叠氮化物是用于区域发散合成有价值的官能化咪唑（产率32 - 98%）和嘧啶衍生物（产率45 - 88%）的关键化合物，且底物范围广泛。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4b4/7418094/589cf91a24f9/Beilstein_J_Org_Chem-16-1915-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4b4/7418094/1fe300be931f/Beilstein_J_Org_Chem-16-1915-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4b4/7418094/21802ca1f91e/Beilstein_J_Org_Chem-16-1915-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4b4/7418094/7e06bc94d1e6/Beilstein_J_Org_Chem-16-1915-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4b4/7418094/943f54d1cbb0/Beilstein_J_Org_Chem-16-1915-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4b4/7418094/d0165d728978/Beilstein_J_Org_Chem-16-1915-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4b4/7418094/589cf91a24f9/Beilstein_J_Org_Chem-16-1915-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4b4/7418094/1fe300be931f/Beilstein_J_Org_Chem-16-1915-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4b4/7418094/21802ca1f91e/Beilstein_J_Org_Chem-16-1915-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4b4/7418094/7e06bc94d1e6/Beilstein_J_Org_Chem-16-1915-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4b4/7418094/943f54d1cbb0/Beilstein_J_Org_Chem-16-1915-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4b4/7418094/d0165d728978/Beilstein_J_Org_Chem-16-1915-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4b4/7418094/589cf91a24f9/Beilstein_J_Org_Chem-16-1915-g007.jpg

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