Base-catalyzed and DMSO-promoted intramolecular hydroalkoxylation to prepare pentacyclic chromeno[4,3-<i>b</i>]indolines

Nie, Chang-Rui; Zhao, Hongping; Liang, Wang-Fu; Zhong, Xia; Liang, Cui; Su, Gui‐Fa; Mo, Dong‐Liang

doi:10.1039/d2gc02225g

Green Chem.

2022

DOI: 10.1039/d2gc02225g

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Base-catalyzed and DMSO-promoted intramolecular hydroalkoxylation to prepare pentacyclic chromeno[4,3-b]indolines

Chang-Rui Nie

Hongping Zhao

Wang-Fu Liang

et al.

Abstract: A base-catalyzed and DMSO-promoted atom economic intramolecular hydroalkoxylation was developed to prepare a variety of pentacyclic chromeno[4,3-b]indolines in good yields with high regioselectivity and diastereoselectivity. Mechanistic studies revealed that DMSO...

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Cited by 4 publications

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References 69 publications

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“…Dimethyl sulfoxide (DMSO) is produced industrially by oxidizing dimethyl sulfide with nitrogen dioxide or dioxygen, and has been widely used in organic chemistry. 6 Apart from being an inexpensive and low-toxic solvent, particularly in oxidative systems, 7 DMSO has been widely employed as an oxidant in well-known named reactions such as the Swern oxidation, 8 and PwtiznerMoffatt oxidation. 9 The nucleophilic nature of the oxygen atom in DMSO towards hard electrophiles has made it a common oxygen source in organic reactions, including the Kornblum reaction.…”

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Alternative method to Baeyer–Villiger oxidation of cyclobutenones using I₂/DMSO catalytic systems

Sun,

Hu,

Peng

et al. 2023

Green Chem.

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confidence: 99%

Alternative method to Baeyer–Villiger oxidation of cyclobutenones using I₂/DMSO catalytic systems

Sun,

Hu,

Peng

et al. 2023

Green Chem.

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Copper(II)‐Catalyzed Cascade Reactions of N‐Aryl Nitrones and Disubstituted Allenoates to Prepare [1,3]Oxazino[3,2‐a]indolines and Dihydropyrido[1,2‐a]indolines

Xin

et al. 2023

Adv Synth Catal

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We described a copper(II)-catalyzed [3 + 2] cycloaddition of N-aryl-α,β-unsaturated nitrones with disubstituted allenoates bifurcated to prepare various [1,3]oxazino[3,2-a]indolines and dihydropyrido[1,2a]indolines in moderate to excellent yields. Mechanistic studies revealed that [1,3]oxazino[3,2-a]indoline was a kinetically favored product and dihydropyrido[1,2-a]indoline was thermodynamically favored product. Moreover, the reaction was easily performed at gram scales and chiral dihydropyrido[1,2-a]indoline could be obtained by using chiral auxiliary. The present method highlights broad substrate scope, good functional group tolerance, and diversity of indoline scaffolds with high diastereoselectivity.

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Dearomative Alkylation-Based Two-Step cis-Diastereoselective Synthesis of Indoline-2,3-Fused Chromans and Tetrahydropyrans

Chouhan,

Ray,

Gogoi

et al. 2024

J. Org. Chem.

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Herein, we describe a two-step, cis-diastereoselective synthesis of indoline-2,3-fused chromans from 3-substituted indoles. The method proceeds without intermediacy of ortho-quinone methides and leverages the dual function of TBS-protected 2-hydroxybenzyl iodides both as highly reactive alkylating agents in a t-BuONa/Et3B-promoted dearomative alkylation step and as a source of masked phenoxide nucleophiles in a subsequent TBAF-induced one-pot deprotection-cyclization step of the resulting indolenines. Importantly, this two-step protocol can also be extended to access indoline-2,3-fused tetrahydropyrans. These syntheses of indoline-2,3-fused chromans and tetrahydropyrans proceed with operational convenience, use easily accessible substrates and reagents, and feature broad substrate scope, high yields and complete diastereoselectivity. Furthermore, the synthesized products have the potential to undergo late-stage functionalization.

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Base-catalyzed and DMSO-promoted intramolecular hydroalkoxylation to prepare pentacyclic chromeno[4,3-b]indolines

Abstract: A base-catalyzed and DMSO-promoted atom economic intramolecular hydroalkoxylation was developed to prepare a variety of pentacyclic chromeno[4,3-b]indolines in good yields with high regioselectivity and diastereoselectivity. Mechanistic studies revealed that DMSO...

Cited by 4 publications

References 69 publications

Alternative method to Baeyer–Villiger oxidation of cyclobutenones using I₂/DMSO catalytic systems

Alternative method to Baeyer–Villiger oxidation of cyclobutenones using I₂/DMSO catalytic systems

Copper(II)‐Catalyzed Cascade Reactions of N‐Aryl Nitrones and Disubstituted Allenoates to Prepare [1,3]Oxazino[3,2‐a]indolines and Dihydropyrido[1,2‐a]indolines

Dearomative Alkylation-Based Two-Step cis-Diastereoselective Synthesis of Indoline-2,3-Fused Chromans and Tetrahydropyrans

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Base-catalyzed and DMSO-promoted intramolecular hydroalkoxylation to prepare pentacyclic chromeno[4,3-b]indolines

Abstract: A base-catalyzed and DMSO-promoted atom economic intramolecular hydroalkoxylation was developed to prepare a variety of pentacyclic chromeno[4,3-b]indolines in good yields with high regioselectivity and diastereoselectivity. Mechanistic studies revealed that DMSO...

Cited by 4 publications

References 69 publications

Alternative method to Baeyer–Villiger oxidation of cyclobutenones using I2/DMSO catalytic systems

Alternative method to Baeyer–Villiger oxidation of cyclobutenones using I2/DMSO catalytic systems

Copper(II)‐Catalyzed Cascade Reactions of N‐Aryl Nitrones and Disubstituted Allenoates to Prepare [1,3]Oxazino[3,2‐a]indolines and Dihydropyrido[1,2‐a]indolines

Dearomative Alkylation-Based Two-Step cis-Diastereoselective Synthesis of Indoline-2,3-Fused Chromans and Tetrahydropyrans

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Alternative method to Baeyer–Villiger oxidation of cyclobutenones using I₂/DMSO catalytic systems

Alternative method to Baeyer–Villiger oxidation of cyclobutenones using I₂/DMSO catalytic systems