Access to thiazoline and spiro[indoline-3,3′-thiophene] scaffolds <i>via</i> a formal [3 + 2] annulation reaction of crotonate-derived sulfur ylides and β-ketothioamides

Zheng, Jing; Gu, Hui; Chen, Qinfang; Yang, Weiran

doi:10.1039/d3ob00087g

Cited by 5 publications

(5 citation statements)

References 39 publications

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“…In 2023, Zheng et al collaborated to identify a novel pathway that dealt with the synthesis of thiazoline and spiro [indoline-3,3 0 -thiophene] scaffolds 223 (Scheme 47) [72]. The scheme proceeded through a [3 + 2] formal annulation reaction involving β-ketothioamides 221 and sulfur ylides 222 obtained from crotonates.…”

Section: Preparation Of Thiazoline and Indoline Thiophene In The Pres...mentioning

confidence: 99%

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Recent advance: Sulfur ylides in organic synthesis

Kumar,

Sadaf,

Pamidighantam

et al. 2023

Journal of Heterocyclic Chem

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Sulfur ylides are versatile structures that display various characteristics and participate in a myriad of reactions to produce simple, effective, and sometimes stereoselective reactions toward synthesizing sulfur‐containing compounds. Nonetheless, their fulfillment tremendous developments have been made in this field in the past few decades. In this comprehensive review, luminosity is illuminated on the application of sulfur ylides involved in various domino, cascade annulation reactions, and carbene trapping reagents with chameleonic reactivity. In the past numerous decennary, chemists have used sulfur ylides in solvent‐dependent, rhodium catalyzed, dealkylative intercepted, photochemical reaction, halotrifluoromethylation, benzannulation, amidation various name reactions such as Mizoroki–Heck, Suzuki–Miyaura, and Sommelet–Hauser rearrangements. Moreover, other prime applications include metal catalysis, epoxidation of carbonyl compounds, acylmethylation, cyclomerization, oxidation, and insertion reactions. Additionally, some sulfur ylides are extremely useful structures that play a major role in the synthesis of various medicinally active heterocycles structural motifs. This review article discusses all these reactions, their proposed mechanisms, and their application in the current scenario, at length. This tutorial review concludes by providing a future outlook on the investigation into sulfur ylides and various other compounds synthesized using it have great potential to be used in industries, laboratories, pharmaceutical companies, drug production, clinical use, medicinal chemistry, and agrochemical purposes.

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Section: Preparation Of Thiazoline and Indoline Thiophene In The Pres...mentioning

confidence: 99%

“…The method was found to be of interest as it provided a simple and inexpensive method to produce biologically active products at a large scale. It was deemed to be of particular importance for pharmaceutical companies (Figure 23) [72]. unsaturated αand β-imines 225 (Scheme 48) [73].…”

Section: Preparation Of Thiazoline and Indoline Thiophene In The Pres...mentioning

confidence: 99%

Recent advance: Sulfur ylides in organic synthesis

Kumar,

Sadaf,

Pamidighantam

et al. 2023

Journal of Heterocyclic Chem

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“…Another possibility to bring a [3 + 2] anellation reaction to fruition for the compound class of aroyl-S,N-ketene acetals has been the anellation of crotonate-derived sulfur ylides and βketothiamides to produce both spiro[indoline-3,3'-thiophenes] but also aroyl-S,N-ketene acetals embedded in indanone or a dihydronaphthalenone in mediocre to excellent yields (Scheme 10, A). [68] Similarly, applying 3-oxo-3-phenylpropanethioamide and reacting it with crotonate-derived sulfur ylides led to the formation of aroyl-S,N-ketene acetals in yields ranging between 47 and 98 % (Scheme 10, B). [68] Aroyl-S,N-ketene acetals bearing both a thiazolidine-4-one and an ethyl acetate sidechain were transformed into tetrahydrofuro[2,3-d]thiazole by first cleaving of the acid ester and a follow-up intramolecular cyclization by using sodium borohydride.…”

Section: Anellated Aroyl-sn-ketene Acetalsmentioning

confidence: 99%

“…[68] Similarly, applying 3-oxo-3-phenylpropanethioamide and reacting it with crotonate-derived sulfur ylides led to the formation of aroyl-S,N-ketene acetals in yields ranging between 47 and 98 % (Scheme 10, B). [68] Aroyl-S,N-ketene acetals bearing both a thiazolidine-4-one and an ethyl acetate sidechain were transformed into tetrahydrofuro[2,3-d]thiazole by first cleaving of the acid ester and a follow-up intramolecular cyclization by using sodium borohydride. Thus, four examples in yields ranging between 30 and 74 % were readily synthesized (Scheme 10, C).…”

Section: Anellated Aroyl-sn-ketene Acetalsmentioning

confidence: 99%

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Aroyl‐S,N‐Ketene Acetals: Luminous Renaissance of a Class of Heterocyclic Compounds

Biesen,

Müller

2023

Chemistry A European J

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Aroyl‐S,N‐ketene acetals represent a peculiar class of heterocyclic merocyanines, compounds bearing pronounced and rather short dipoles with great push‐pull characteristics that define their rich properties. They are accessible via a wide array of synthetic concepts and procedures, ranging from addition‐elimination and condensation procedures up to rearrangement and metal‐mediated reactions. With our work from 2020, aroyl‐S,N‐ketene acetals have been identified as powerful and promising dyes with pronounced and vastly tunable solid‐state emission and aggregation‐induced emission properties. One characteristic trademark of this class of dye molecules is the level of control that could be exerted, and which was thoroughly explored. Based on these results, the field was opened to extend the system to bi‐ and multichromophoric systems by the full toolkit of synthetic organic chemistry thus giving access to even more exciting properties and manifolded substance libraries capitalizing on the AIE properties. This review aims at outlining the reaction‐based principles that allow for a swift and facile access to aroyl‐S,N‐ketene acetals, their methodical and structural evolution and the plethora of fluorescence and aggregation properties.

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TBHP‐Mediated Intermolecular Radical Coupling and Intramolecular Cyclization Cascade: Access to Furo[2,3‐b]quinoxalines and Their Photophysical Study

Ray,

Kumar,

Singh

et al. 2023

Adv Synth Catal

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A cascade one‐pot strategy to construct 31 examples of furo‐fused quinoxalines in up to 88% yields has been devised from readily accessible β‐ketothioamides and quinoxalin‐2‐ones in open flask at room temperature under TBHP mediated conditions. Mechanistic studies revealed that the overall reactivity relies on the seamless integration of intermolecular radical coupling and intramolecular cyclization via desulfhydration of C=S bond cleavage. Generation of H2S as the only by‐product makes this process highly attractive. Furthermore, the photophysical behavior of the furo‐fused quinoxalines has also been studied.

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Access to thiazoline and spiro[indoline-3,3′-thiophene] scaffolds via a formal [3 + 2] annulation reaction of crotonate-derived sulfur ylides and β-ketothioamides

Abstract: A formal [3+2] annulation reaction of crotonate-derived sulfur ylides and β-Ketothioamides (KTAs) was developed successfully to produce good to excellent yields of thiazoline and spiro[indoline-3,3'-thiophen] scaffolds. This transformation is a...

Cited by 5 publications

References 39 publications

Recent advance: Sulfur ylides in organic synthesis

Recent advance: Sulfur ylides in organic synthesis

Aroyl‐S,N‐Ketene Acetals: Luminous Renaissance of a Class of Heterocyclic Compounds

TBHP‐Mediated Intermolecular Radical Coupling and Intramolecular Cyclization Cascade: Access to Furo[2,3‐b]quinoxalines and Their Photophysical Study

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