Donor-Acceptor Cyclopropane Ring Opening with 6-Amino-1,3-dimethyluracil and Its Use in Pyrimido[4,5-b]azepines Synthesis

被引：14

作者：

Vartanova, Anna E. ^{[1
,2
]}

Levina, Irina I. ^{[3
]}

Rybakov, Victor B. ^{[4
]}

Ivanova, Olga A. ^{[1
,4
]}

Trushkov, Igor, V ^{[1
,5
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119334, Russia

[2] RUDN Univ, Fac Sci, Moscow 117198, Russia

[3] Russian Acad Sci, NM Emanuel Inst Biochem Phys, Moscow 119334, Russia

[4] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

[5] Dmitry Rogachev Natl Res Ctr Pediat Hematol Oncol, Lab Chem Synth, Moscow 117997, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 17期

基金：

俄罗斯科学基金会;

关键词：

FRIEDEL-CRAFTS ALKYLATION; FORMAL 3+2 CYCLOADDITION; BRONSTED ACID; CONSTRUCTION; ANNULATION; CYCLOPENTANNULATION; 1,1-DIESTERS; DERIVATIVES; INHIBITORS; CATALYST;

D O I：

10.1021/acs.joc.1c01064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A scandium trifluoromethanesulfonate-catalyzed reaction of donor-acceptor cyclopropanes with 6-amino-1,3-dimethyluracil was found to proceed as three-membered ring opening via nucleophilic attack of the C(5) atom of an ambident nucleophile serving as an enamine equivalent. It was shown that, under basic conditions, the obtained products underwent cyclization to 6,7-dihydro-1H-pyrimido[4,5-b]-azepine-2,4,8-triones, an interesting subclass of nucleobase analogues.

引用

页码：12300 / 12308

页数：9

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