Iron Catalyzed Formal [3+2] Cycloaddition of Tetrahydroisoquinoline Affording Amide-bearing Dihydropyrrolo[2,1-a]isoquinolines

Si-Wei Liu; Dan-Dan Ma; Xin-Xin Zhu; Cheng-Dan Luo; Hui-Lin Tan; Xiao-Li Ju; Xue Tan; Xiao-Hui Tang; Jie Huang; Jia Wang; Xian-Xun Wang; Hai-Lei Cui

doi:10.26434/chemrxiv.12015651.v1

Organic Chemistry

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Iron Catalyzed Formal [3+2] Cycloaddition of Tetrahydroisoquinoline Affording Amide-bearing Dihydropyrrolo[2,1-a]isoquinolines

Working Paper

Si-Wei Liu Chongqing University of Arts and Sciences ,
Dan-Dan Ma ,
Xin-Xin Zhu ,
Cheng-Dan Luo ,
Hui-Lin Tan ,
Xiao-Li Ju ,
Xue Tan ,
Xiao-Hui Tang ,
Jie Huang ,
Jia Wang ,
Xian-Xun Wang ,
Hai-Lei Cui

Abstract

We have developed an iron(III) chloride hexahydrate catalyzed formal [3+2] cycloaddition of tetrahydroisoquinolines with amide group-bearing Morita-Baylis-Hillman (MBH) carbonates. A range of highly functionalized dihydropyrrolo[2,1-a]isoquinolines could be prepared through SN2’/oxidation/ electrocyclization/aromatization cascade (32-62% yield).