Issue 2, 2023
From the journal:

Organic Chemistry Frontiers

Selective construction of spiro[indoline-3,5′-pyrrolo[3,4-b]azepines] and spiro[indoline-3,3′-pyrroles] via a [4 + 3]/[3 + 2] cycloaddition reaction of α,β-unsaturated aldimines and MBH adducts of isatins†

Dan Liu,a   Jing Sun,a   Qiu Suna  and  Chao-Guo Yan ORCID logo *a  

* Corresponding authors

a College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China
E-mail: cgyan@yzu.edu.cn

Abstract

An efficient synthetic protocol for the selective construction of spiro[indoline-3,5′-pyrrolo[3,4-b]azepines] and spiro[indoline-3,3′-pyrroles] via a cycloaddition reaction of α,β-unsaturated aldimines and MBH adducts of isatins was successfully developed. DABCO facilitated the cycloaddition of α,β-unsaturated N-arylaldimines and MBH maleimides of isatins, affording spiro[indoline-3,5′-pyrrolo[3,4-b]azepines] with high yields and diastereoselectivity via a [4 + 3] cycloaddition process. On the other hand, the annulation reaction of α,β-unsaturated N-arylaldimines and MBH acrylates or nitriles of isatins resulted in spiro[indoline-3,3′-pyrroles] through a [3 + 2] cycloaddition process.

Graphical abstract: Selective construction of spiro[indoline-3,5′-pyrrolo[3,4-b]azepines] and spiro[indoline-3,3′-pyrroles] via a [4 + 3]/[3 + 2] cycloaddition reaction of α,β-unsaturated aldimines and MBH adducts of isatins

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Article information

DOI
https://doi.org/10.1039/D2QO01771G
Article type
Research Article
Submitted
08 Nov 2022
Accepted
09 Dec 2022
First published
10 Dec 2022

Org. Chem. Front., 2023,10, 540-547

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Selective construction of spiro[indoline-3,5′-pyrrolo[3,4-b]azepines] and spiro[indoline-3,3′-pyrroles] via a [4 + 3]/[3 + 2] cycloaddition reaction of α,β-unsaturated aldimines and MBH adducts of isatins

D. Liu, J. Sun, Q. Sun and C. Yan, Org. Chem. Front., 2023, 10, 540 DOI: 10.1039/D2QO01771G

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