2022
DOI: 10.1002/ajoc.202200288
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Base‐promoted Oxidative Sulfuration/Cyclization to Construct Naphtho[2,3‐d]thiazole through Three‐component Reaction Using S8 as the Sulfur Source

Abstract: A base‐promoted three‐component oxidative sulfuration/cyclization reaction of 2‐amino‐1,4‐naphthoquinone, aldehyde and elemental sulfur was developed. The naphtho[2,3‐d]thiazole ring was determined by forming two C−S bonds and one C=N bond, which demonstrates the advantages of cheap raw materials, no transition metal, and economic efficiency. The substrate scope was broad with aromatic and aliphatic aldehydes. The mechanistic study might promote the reaction design for a oxidative sulfuration/cyclization react… Show more

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Cited by 7 publications
(7 citation statements)
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“…2-Aminonaphthalene-1,4-dione R1 was obtained in one step by reaction of 1,4-naphthoquinone and sodium azide NaN 3 in acidic conditions and isolated in 64% yield . To obtain the precursor R6 of oxime ester OXE-0, a treatment of 1 equiv of R1 with 1 equiv of 4-(1,3-dioxolan-2-yl)-2,5-bis­(dodecyloxy)­benzaldehyde R2 in the presence of sulfur S8 and sodium hydrogenocarbonate NaHCO 3 was carried out according to the literature . Unfortunately, no trace of the expected product R6 was detected in the reaction mixture by 1 H NMR.…”
Section: Resultsmentioning
confidence: 99%
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“…2-Aminonaphthalene-1,4-dione R1 was obtained in one step by reaction of 1,4-naphthoquinone and sodium azide NaN 3 in acidic conditions and isolated in 64% yield . To obtain the precursor R6 of oxime ester OXE-0, a treatment of 1 equiv of R1 with 1 equiv of 4-(1,3-dioxolan-2-yl)-2,5-bis­(dodecyloxy)­benzaldehyde R2 in the presence of sulfur S8 and sodium hydrogenocarbonate NaHCO 3 was carried out according to the literature . Unfortunately, no trace of the expected product R6 was detected in the reaction mixture by 1 H NMR.…”
Section: Resultsmentioning
confidence: 99%
“…40 To obtain the precursor R6 of oxime ester OXE-0, a treatment of 1 equiv of R1 with 1 equiv of 4-(1,3-dioxolan-2-yl)-2,5-bis(dodecyloxy)benzaldehyde R2 in the presence of sulfur S8 and sodium hydrogenocarbonate NaHCO 3 was carried out according to the literature. 38 Unfortunately, no trace of the expected product R6 was detected in the reaction mixture by 1 H NMR. Instead of R6, another product was obtained despite the use of 1:1 ratio between the aminonaphthoquinone and the aldehyde, namely, the difunctional product 2,2′-(2,5-bis(dodecyloxy)-1,4phenylene)bis(naphtho[2,3-d]thiazole-4,9-dione) R3 that was isolated in low yield (19%).…”
Section: ■ Introductionmentioning
confidence: 99%
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“…Fascinated by the immense pharmacological profiles of pyrazole, thioamide and amide derivatives, it was envisaged to develop a practical approach towards the synthesis of pyrazolethioamide and pyrazole-amide conjugates. Elemental sulfur was explored as a sulfurating reagent for the generation of thioamides owing to its nontoxic, odorless nature and versatile reactivity profile [65][66][67][68][69][70][71][72][73][74][75][76]. To the best of our knowledge, the syntheses of pyrazole C-3/4/5-linked thioamide and amide conjugates have not been reported.…”
Section: Introductionmentioning
confidence: 99%