Copper(II)‐Mediated Homocoupling of Thioamides for the Synthesis of 1,2,4‐Thiadiazoles

Sun, Yan; Wu, Wanqing; Jiang, Huanfeng

doi:10.1002/ejoc.201402194

Cited by 21 publications

(7 citation statements)

References 42 publications

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“…In this case, Cu(II) serves as a catalyst to catalyze the formation of C–S bond. In comparison with other counterions, -OTf can be easily exchanged …”

Section: Resultsmentioning

confidence: 99%

Copper-Catalyzed Domino-Double Annulation of o-Aminobenzamides with 2-Iodoisothiocyanates for the Synthesis of 12H-Benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones

Wu,

Yang,

Wang

et al. 2024

J. Org. Chem.

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A facile and efficient copper-catalyzed domino-double annulation strategy was developed from easily accessible o-aminobenzamides and 2-iodoisothiocyanates, which affords a direct pathway for the synthesis of tetracyclic fused 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones in moderate to good yields without the addition of ligands, bases, and external oxidants. The reaction involves a C–N bond cleavage and the formation of a C–N/C–S bond in one step with the advantages of using an inexpensive copper catalyst and easy operation. Mechanistic studies suggest that this transformation proceeds via intermolecular condensation of o-aminobenzamides with 2-iodoisothiocyanates, followed by an intramolecular Ullmann-type cross-coupling cyclization reaction.

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“…In this case, Cu(II) serves as a catalyst to catalyze the formation of C–S bond. In comparison with other counterions, -OTf can be easily exchanged …”

Section: Resultsmentioning

confidence: 99%

Copper-Catalyzed Domino-Double Annulation of o-Aminobenzamides with 2-Iodoisothiocyanates for the Synthesis of 12H-Benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones

Wu,

Yang,

Wang

et al. 2024

J. Org. Chem.

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“…Consequently, a plausible biosynthetic pathway of 1 from 2 was suggested as shown in Scheme 1 and further established the formation of the 1,2,4-thiadiazole moiety, but neither 1,2,3-, 1,3,4-, nor 1,2,5-thiadiazole, as a linking unit in the molecule of 2 . Finally, a comparison of the NMR data of compound 2 with those of a synthetic product prepared by copper(II)-mediated homocoupling of thioamides revealed the same chemical identity [ 37 ]. However, the full assignment of 1 H and 13 C NMR signals was reported herein by the analysis of 2D NMR correlations for the first time.…”

Section: Resultsmentioning

confidence: 99%

The Invasive Anemone Condylactis sp. of the Coral Reef as a Source of Sulfur- and Nitrogen-Containing Metabolites and Cytotoxic 5,8-Epidioxy Steroids

et al. 2023

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The Condylactis-genus anemones were examined for their proteinaceous poisons over 50 years ago. On the other hand, the current research focuses on isolating and describing the non-proteinaceous secondary metabolites from the invasive Condylactis anemones, which help take advantage of their population outbreak as a new source of chemical candidates and potential drug leads. From an organic extract of Condylactis sp., a 1,2,4-thiadiazole-based alkaloid, identified as 3,5-bis(3-pyridinyl)-1,2,4-thiadiazole (1), was found to be a new natural alkaloid despite being previously synthesized. The full assignment of NMR data of compound 1, based on the analysis of 2D NMR correlations, is reported herein for the first time. The proposed biosynthetic precursor thionicotinamide (2) was also isolated for the first time from nature along with nicotinamide (3), uridine (5), hypoxanthine (6), and four 5,8-epidioxysteroids (7–10). A major secondary metabolite (−)-betonicine (4) was isolated from Condylactis sp. and found for the first time in marine invertebrates. The four 5,8-epidioxysteroids, among other metabolites, exhibited cytotoxicity (IC50 3.5–9.0 μg/mL) toward five cancer cell lines.

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“…In both cases, mixture of products was obtained in different ratio (27:28 = 5:4 and 29:30 = 5:1 respectively) (Table 2). Substrates with an axial [8] 15 78 2 2 12 [16] 15 75 3 3 13 [17] 10 52 4 4 14 [7] 08 73 5 5 15 [7] 15 69 6 6 16…”

Section: Resultsmentioning

confidence: 99%

Facile Transformation of Nitriles into Thioamides: Application to C‐Glycosyl Nitrile Derivatives

Ghosh

Misra

2017

ChemistrySelect

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An effective reaction condition for the rapid transformation of nitrile derivatives into thioamide derivatives has been developed by the treatment with a combination of carbon disulfide and sodium sulfide. The reaction condition is equally effective for the transformation of alkyl, aryl nitriles. C‐Glycosyl nitriles also furnished C‐glycosyl thioamide derivatives in satisfactory yield under the reported reaction condition. The reaction condition is simple, high yielding and suitable for scaled up.

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Copper(II)‐Mediated Homocoupling of Thioamides for the Synthesis of 1,2,4‐Thiadiazoles

Cited by 21 publications

References 42 publications

Copper-Catalyzed Domino-Double Annulation of o-Aminobenzamides with 2-Iodoisothiocyanates for the Synthesis of 12H-Benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones

Copper-Catalyzed Domino-Double Annulation of o-Aminobenzamides with 2-Iodoisothiocyanates for the Synthesis of 12H-Benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones

The Invasive Anemone Condylactis sp. of the Coral Reef as a Source of Sulfur- and Nitrogen-Containing Metabolites and Cytotoxic 5,8-Epidioxy Steroids

Facile Transformation of Nitriles into Thioamides: Application to C‐Glycosyl Nitrile Derivatives

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