An intramolecular Diels-Alder reaction in the synthesis of N-aroyl-3a,6-epoxyisoindole-2-carbothioamides

被引：0

作者：

Mertsalov, Dmitriy F. ^{[1
]}

Lovtsevich, Lala V. ^{[1
]}

Shchevnikov, Dmitriy M. ^{[1
]}

Dobrushina, Yulya M. ^{[1
]}

Sorokina, Elena A. ^{[1
]}

Grigoriev, Mikhail S. ^{[2
]}

Zaytsev, Vladimir P. ^{[1
]}

机构：

[1] RUDN Univ, 6 Miklukho Maklaya St, Moscow 117198, Russia

[2] Russian Acad Sci, Frumkin Inst Phys Chem & Electrochem, 31 Build,4 Leninsky Ave, Moscow 119071, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2024年 / 60卷 / 9-10期

基金：

俄罗斯科学基金会;

关键词：

allylamine; epoxyisoindole; furfurylamine; isothiocyanate; thiourea; IMDAF reaction; intramolecular [4+2] cycloaddition; TRICYCLIC NITROGEN-HETEROCYCLES; CYCLOADDITION; COMPLEXES; THIOUREA; TANDEM; IMDAF;

D O I：

10.1007/s10593-024-03369-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of allyl(furfuryl)amines with aroyl isothiocyanates was studied. The reaction proceeded via an initial nucleophilic addition of the allylamine nitrogen atom to isothiocyanates and a subsequent spontaneous intramolecular Diels-Alder reaction involving the furan ring of intermediate N-allyl-N-furfurylthioureas with the formation of a single diastereomer of 3a,6-epoxyisoindoles.

引用

页码：512 / 523

页数：12

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