A general synthesis of benzofuran-2-thiolates via intramolecular addition of phenolates to alkynethiolates

D'hooge, B.; Smeets, Stefan; Toppet, Suzanne; Dehaen, Wim

doi:10.1039/a704025c

Cited by 27 publications

(7 citation statements)

References 5 publications

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“…Remarkable differences are known to exist between Se- and S-containing compounds. Due to the larger size of the Se-atom, selenium compounds show an increased polarizability and therefore they are, in general, less stable than the corresponding S-analogues [ 17 , 18 , 19 , 20 ]. We report herein on our efforts to generate the multi-branched benzene derivatives 1a, 1b, 1c and 1d , in which the 1,2,3-selenadiazole rings are linked to the central benzene core via phenoxymethylene spacers.…”

Section: Introductionmentioning

confidence: 99%

New Multi-1,2,3-Selenadiazole Aromatic Derivatives

Al-Smadi

Ratrout

2005

Molecules

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The aromatic polyketones 3a-d are versatile compounds for the synthesis of the multi-1,2,3-selenadiazole aromatic derivatives 1a-d. The preparation starts with the reaction between the multi-bromomethylene benzene derivatives 2a-d and 4-hydroxy-acetophenone to give compounds 3a-d which are transformed through the reaction with semicarbazide hydrochloride or ethyl hydrazine carboxylate into the corresponding semicarbazones derivatives 4a-d or hydrazones 5a-d. The reaction with selenium dioxide leads to regiospecific ring closure of semicarbazones or hydrazones to give the multi-1,2,3-selenadiazole aromatic derivatives in high yield.

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Section: Introductionmentioning

confidence: 99%

New Multi-1,2,3-Selenadiazole Aromatic Derivatives

Al-Smadi

Ratrout

2005

Molecules

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“…Due to the large size of the Seatom. Selenium compounds show an increased polarizability and therefore they are in general, less stable than the Sanalogues [14][15][16][17].…”

Section: J Heterocyclic Chem 41 887 (2004)mentioning

confidence: 99%

New many fold 1,2,3‐selenadiazole aromatic derivatives

Al-Smadi

Ratrout

2004

Journal of Heterocyclic Chem

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The many fold aromatic ketones 2a‐d are versatile compounds for the synthesis of the many fold 1,2,3‐selenadiazole aromatic derivatives 5a‐d. The preparation starts with the reaction between the many fold bromomethylene benzene derivatives 1a‐d and 4‐hydroxyacetophenone, which are transformed through the reaction with semicarbazide hydrochloride or ethylhydrazine carboxylate into the corresponding semicarbazones derivatives 3a‐d or hydrazones 4a‐d. The reaction with selenium dioxide leads to regiospecific ring closure of semicarbazones or hydrazones to give the many fold 1,2,3‐selenadiazole aromatic derivatives in high yield.

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“…Only when the very reactive methyl iodide was added, some O-alkylated product 211 was formed. 84,85 We proved by 1 To apply this methodology for the formation of nitrogen heterocycles, we have studied the base-catalyzed ring cleavage of 1,2,3-thiadiazole-4-carbonylhydrazide derivatives 219. Thus, when benzoyl and tosyl derivatives of 219 were treated with 1 equiv of t-BuOK followed by alkylation with 1 equiv of alkyl halogenides, the pyrazoles 220 were obtained in moderate yields.…”

Section: Base-catalyzed Decompositionmentioning

confidence: 99%