Highly selective Diels-Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole

被引：4

作者：

Escalante, Carlos H. ^{[1
]}

Martinez-Mora, Eder, I ^{[1
,2
]}

Espinoza-Hicks, Carlos ^{[3
]}

Camacho-Davila, Alejandro A. ^{[3
]}

Ramos-Morales, Fernando R. ^{[4
]}

Delgado, Francisco ^{[1
]}

Tamariz, Joaquin ^{[1
]}

机构：

[1] Inst Politecn Nacl, Dept Quim Organ, Escuela Nacl Ciencias Biol, Prolongac Carpio & Plan Ayala S-N, Mexico City 11340, DF, Mexico

[2] Univ Autonoma Coahuila, Fac Ciencias Quim, Dept Quim Organ, Blvd Venustiano Carranza & Ingn J Cardenas S-N, Saltillo 25280, Coahuila, Mexico

[3] Univ Autonoma Chihuahua, Fac Ciencias Quim, Dept Quim Organ, Circuito Univ S-N, Chihuahua 31125, Chih, Mexico

[4] Univ Veracruzana, Unidad Serv Apoyo Resoluc Analit, Luis Castelazo Ayala S-N, Xalapa 91190, Veracruz, Mexico

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 16卷

关键词：

endo-Diels-Alder stereocontrol; 2-formylpyrrole; intramolecular Heck arylation reaction; non-covalent interactions; pyrroloindoles; pyrroloisoindoles; SECONDARY ORBITAL INTERACTIONS; NONCOVALENT INTERACTIONS; ORIGIN; ENDO; CYCLOPENTADIENE; FUNCTIONALS; REACTIVITY; STACKING; PRODUCTS; ANALOGS;

D O I：

10.3762/bjoc.16.113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly regio-, chemo- and stereoselective divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles is herein described, starting from 2-formylpyrrole and employing Diels-Alder and Heck arylation reactions. 3-(N-Benzyl-2-pyrrolyl)acrylates and 4-(pyrrol-2-yl)butenones underwent a highly endo-Diels-Alder cycloaddition with maleimides to furnish octahydropyrrolo[3,4-]indoles, which served as precursors in the regioselective synthesis of aza-polycyclic skeletons via an intramolecular Heck arylation reaction. Through the latter reaction, the 3-(N-benzyl-2-pyrrolyl)acrylates give rise to 3-(pyrrolo[2,1-a] isoindol-3-yl)acrylates. A further oxidative aromatization of the polycyclic intermediates provides the corresponding polycyclic pyrrolo-isoindoles and isoindolo-pyrrolo-indoles. A theoretical study on the stereoselective Diels-Alder reactions, carried out by calculating the endo/exo transition states, revealed the assistance of non-covalent interactions in governing the endo stereocontrol.

引用

页码：1320 / 1334

页数：15

共 85 条

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