Palladium‐Catalyzed 3‐Aryl‐5‐acyl‐1,2,4‐thiadiazole Formation from Ketones, Amidines, and Sulfur Powder

Wang, Zilong; Xie, Hao; Xiao, Fuhong; Guo, Yanjun; Huang, Huawen; Deng, Guo‐Jun

doi:10.1002/ejoc.201700148

Cited by 24 publications

(6 citation statements)

References 52 publications

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“…In this context, multicomponent synthesis and cascade reactions show great potential to provide opportunities for rapid preparation of target compounds through predesigned routes . To develop facile synthesis of functionalized heterocycles, we have contributed a number of examples of multicomponent reactions including sulfur‐involved synthesis of phenothiazines, benzothiophenes, thiadiazoles,, and benzothiazoles. Herein, we disclose the novel self‐assembly of arylacetaldehydes, elemental sulfur, and 1,3‐dicarbonyls to access 2,3,5‐trisubstituted thiophenes under base conditions.…”

Section: Optimization Of the Reaction Conditions[a]mentioning

confidence: 99%

One‐Pot Synthesis of 2,3,5‐Trisubstituted Thiophenes through Three‐Component Assembly of Arylacetaldehydes, Elemental Sulfur, and 1,3‐Dicarbonyls

Wang

Xiao

et al. 2018

Adv Synth Catal

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Section: Optimization Of the Reaction Conditions[a]mentioning

confidence: 99%

One‐Pot Synthesis of 2,3,5‐Trisubstituted Thiophenes through Three‐Component Assembly of Arylacetaldehydes, Elemental Sulfur, and 1,3‐Dicarbonyls

Wang

Xiao

et al. 2018

Adv Synth Catal

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“…9c Inspired by the Willgerodt-Kindler reaction, Deng and co-workers further developed an efficient method to access 3,5-disubstituted 1,2,4-thiadiazoles from amidines, acetophenones, and elemental sulfur under palladium-catalyzed reaction conditions (Scheme 47b). 79 In this transformation, aromatic ketones acted as both the carbon and acyl sources.…”

Section: Cluster Synlettmentioning

confidence: 99%

Recent Advances in Sulfur-Containing Heterocycle Formation via Direct C–H Sulfuration with Elemental Sulfur

Liu

Deng

Huang

2020

Synlett

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The synthesis of sulfur heterocycles via the construction of C–S bonds has received considerable attention due to their biological value and extensive pharmaceutical application. While diverse sulfurating agents have been developed over the past few decades, in this regard, elemental sulfur, with advantages of low toxicity, odorless nature and chemical stability, has great potential for the construction of diverse sulfur heterocycles through its direct incorporation into the target molecules in a concise way. Direct functionalization of inert C–H bonds can shorten the number of reaction steps and minimize the amount of waste formed. Hence, heteroannulations via direct C–H sulfuration is considered to be an attractive strategy for the synthesis of sulfur heterocycles. In the last few years, a vast array of concise systems have been reported for the synthesis of some valuable sulfur heterocycles such as thiophenes, thienoindoles, thienothiazoles, thiazoles, benzothiazoles, and thiadiazoles through direct C–H sulfuration/annulations with elemental sulfur. These are discussed in detail in this review.1 Introduction2 Thiophenes3 Thienoindoles4 Thienothiazoles5 Other Fused Thiophenes6 Thiazoles7 Benzothiazoles8 Thiadiazoles9 Others10 Summary and Outlook

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“…Later the authors developed a methodology involving the use of elemental sulfur to construct the 1,2,4‐thiadiazole ring with the aid of an arylketone/amidine/sulfur combination in the presence of PdCl 2 /K 2 HPO 4 …”

Section: Synthesis Of Heterocyclesmentioning

confidence: 99%

Oxidative Coupling with S–N Bond Formation

2018

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Oxidative strategies are a powerful tool in organic synthesis for the formation of heteroatom–heteroatom, carbon–heteroatom, and carbon–carbon bonds. Among these processes the reactions of oxidative S–N bond formation deserve considerable interest as convenient, effective, and environmentally friendly alternatives to existing methods for the synthesis of a great variety of organic compounds widely used in organic and medicinal chemistry. These transformations take place through the interaction of S‐ and N‐reagents and an oxidant, by radical or ionic mechanisms. Sulfinic acids and their salts, thiols, sulfonyl hydrazides, and thiosulfonates are generally used as S‐reagents; aliphatic and aromatic amines are usually applied as N‐reagents. The role of the oxidant mostly lies in the oxidation of the S‐reagent, after which the formed active species reacts with the N‐reagent to result in the S–N coupling product. There are two versions of oxidative S–N coupling processes: the intermolecular variant opens simple pathways to sulfen‐, sulfin‐, and sulfonamides, sulfenyl‐ and sulfoximines, sulfanes, and sulfur diimides, whereas the intramolecular one leads to the formation of various heterocycles. Of the major problems associated with successful performance of oxidative S–N coupling reactions, the first relates to the search for coupling partners that will work together to form a new bond under oxidative conditions. The second is the choice of a suitable oxidative system that will not overoxidize starting compounds. That is why mild oxidants, such as hypervalent iodine compounds and copper salts and complexes, are generally applied in these processes. This is the first exhaustive review relating to achievements in oxidative transformations involving S–N bond formation. It summarizes 134 references, mainly from 2000 to 2018, and is divided into chapters according to the classes of compounds synthesized.

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Palladium‐Catalyzed 3‐Aryl‐5‐acyl‐1,2,4‐thiadiazole Formation from Ketones, Amidines, and Sulfur Powder

Cited by 24 publications

References 52 publications

One‐Pot Synthesis of 2,3,5‐Trisubstituted Thiophenes through Three‐Component Assembly of Arylacetaldehydes, Elemental Sulfur, and 1,3‐Dicarbonyls

One‐Pot Synthesis of 2,3,5‐Trisubstituted Thiophenes through Three‐Component Assembly of Arylacetaldehydes, Elemental Sulfur, and 1,3‐Dicarbonyls

Recent Advances in Sulfur-Containing Heterocycle Formation via Direct C–H Sulfuration with Elemental Sulfur

Oxidative Coupling with S–N Bond Formation

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