Syntheses of 4-allyl-/4-allenyl-4-(arylthio)-1,4-dihydroisoquinolin-3-ones <i>via</i> the photochemical Doyle–Kirmse reaction

Xie, Jianwei; Suleman, Muhammad; Wang, Zaibin; Mao, Xinfei; Mao, Beibei; Fan, Jiale; Lü, Ping; Wang, Yanguang

doi:10.1039/d1ob00859e

Cited by 8 publications

(6 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…115 While these studies mainly focus on employing aryl diazoacetates, in 2021, Lu and Wang expanded the scope of diazo compounds to 4-diazo-1,4-dihydroisoquinolin-3-ones, which participate in reactions with both allyl and propargyl sulfides. 116 The Sommelet−Hauser rearrangement was observed in sulfonium ylides obtained from the reaction of α-mercapto esters and free carbenes. In 2019, Koenigs and co-workers revealed the photochemical synthesis of various alkylated arenes 43.3 from aryl diazoacetates 43.1 and α-mercapto esters 43.2 (Scheme 43A).…”

Section: Si−h Insertionsmentioning

confidence: 99%

“…In 2020, Gryko’s group demonstrated the use of propargyl sulfides 42.17 for synthesis of allenes 42.18 – 42.22 (Scheme c) . While these studies mainly focus on employing aryl diazoacetates, in 2021, Lu and Wang expanded the scope of diazo compounds to 4-diazo-1,4-dihydroisoquinolin-3-ones, which participate in reactions with both allyl and propargyl sulfides …”

Section: Diazo Compounds As Singlet Carbene Precursorsmentioning

confidence: 99%

See 1 more Smart Citation

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors

Zhang,

Gevorgyan

2024

Chem. Rev.

View full text Add to dashboard Cite

In recent years, visible light-induced reactions of diazo compounds have attracted increasing attention in organic synthesis, leading to improvement of existing reactions, as well as to the discovery of unprecedented transformations. Thus, photochemical or photocatalytic generation of both carbenes and radicals provide milder tools toward these key intermediates for many valuable transformations. However, the vast majority of the transformations represent new reactivity modes of diazo compounds, which are achieved by the photochemical decomposition of diazo compounds and photoredox catalysis. In particular, the use of a redox-active photocatalysts opens the avenue to a plethora of radical reactions. The application of these methods to diazo compounds led to discovery of transformations inaccessible by the classical reactivity associated with carbenes and metal carbenes. In most cases, diazo compounds act as radical sources but can also serve as radical acceptors. Importantly, the described processes operate under mild, practical conditions. This Review describes this subfield of diazo compound chemistry, particularly focusing on recent advancements.

show abstract

Section: Si−h Insertionsmentioning

confidence: 99%

Section: Diazo Compounds As Singlet Carbene Precursorsmentioning

confidence: 99%

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors

Zhang,

Gevorgyan

2024

Chem. Rev.

View full text Add to dashboard Cite

show abstract

“…We reasoned that a similar strategy could be adopted for the preparation of 1,2,4-trisubsti- tuted 1,4-DHIQs 9 if access to their diazo precursors 10 was gained. N-Sulfonyl analogs of compounds 10 have recently been synthesized via an innovative Dimroth rearrangement of 4-diazoisochroman-3-imines [13] and employed in several acid-and metal-promoted transformations by Lu, Wang et al [14][15][16][17][18]. However, preparation of precursor 10 by direct diazo transfer onto the methylene group of readily available [19,20] 3(2H)-isoquinolones 11 has not been described in the literature.…”

Section: Introductionmentioning

confidence: 99%

Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold

Dar’in¹,

Kantin²,

Bunev³

et al. 2022

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

A practically convenient and streamlined protocol for the trans-diastereoselective introduction of an aryl substituent at position 4 of the 1,4-dihydroisoquinol-3-one (1,4-DHIQ) scaffold is presented. The protocol involves direct Regitz diazo transfer onto readily available 3(2H)-isoquinolones followed by TfOH-promoted hydroarylation by an arene molecule. Screening of the novel 1,2,4-trisubstituted 1,4-DHIQs against cancer cell lines confirmed high cytotoxicity of selected analogs, which validates this new chemotype for further investigations as anticancer cytotoxic agents.

show abstract

“…10 However, most Doyle–Kirmse reactions use ester-derived diazo reagents, 11 and few cases use heterocyclic diazo reagents. 12 Considering the great interest in the oxindole nucleus as the structural motif of many biologically active compounds and clinically used pharmaceuticals, and as part of our ongoing study on the development of efficient Rh( ii ) catalytic chemistry, 13 we envisaged that N–H unprotected diazoindolinones could be transferred into metal carbene intermediates efficiently under a low catalyst-loading Rh( ii ) catalyst, which subsequently undergoes the Doyle–Kirmse reaction exclusively. Allyl sulfides act as both sulfenylating and allylating reagents, and facilely furnish modified C-3 bifunctional 3-allyl-3-(phenylthio)indolin-2-ones (Scheme 1c).…”

Section: Introductionmentioning

confidence: 99%