A new route to 3,4-disubstituted tetrahydrothiophenes

Elall, Eatedal H. M. Abd; Ashmawy, M. I. Al; Mellor, John M.

doi:10.1039/c39870001577

Cited by 14 publications

(4 citation statements)

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“…16−18 Although the ring opening of thiazolidinones is known under aqueous conditions (vide supra), alcoholysis reactions are rare. Mellor and co-workers have reported the conversion of 4-vinyl thiazolidinones to methyl carbamates using potassium hydroxide in methanol, 19 but these conditions gave no identifiable products in the case of our cyclohexenyl derivative 12. The use of sodium or potassium methoxide in methanol at various temperatures similarly led only to decomposition of the starting material.…”

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confidence: 79%

“…According to our initial hypothesis, the ring rearrangement requires the attack of methanol on the thiazolidinone carbonyl, followed by elimination and conjugate addition of the thiol to the enone functionality via a 6- endo -trig process, a known but rare process. − Although the ring opening of thiazolidinones is known under aqueous conditions (vide supra), alcoholysis reactions are rare. Mellor and co-workers have reported the conversion of 4-vinyl thiazolidinones to methyl carbamates using potassium hydroxide in methanol, but these conditions gave no identifiable products in the case of our cyclohexenyl derivative 12 . The use of sodium or potassium methoxide in methanol at various temperatures similarly led only to decomposition of the starting material.…”

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confidence: 99%

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Origin of the Thiopyrone CTP-431 “Unexpectedly” Isolated from the Marine Sponge Cacospongia mycofijiensis

et al. 2018

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An intriguing hypothesis that latrunculin A, a well-known natural product, might have undergone transformation into the unprecedented thiopyrone CTP-431 upon long-term storage in methanol is advanced. Thus, opening of the hemiacetal of latrunculin A, followed by E1CB elimination, and dehydration would give a polyene that could undergo intramolecular Diels-Alder reaction, followed by methanolysis of the thiazolidinone ring and ring closure by intramolecular thiol addition to an enone. Experimental evidence that the novel thiazolidinone to thiopyrone rearrangement can occur is presented.

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confidence: 79%

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confidence: 99%

Origin of the Thiopyrone CTP-431 “Unexpectedly” Isolated from the Marine Sponge Cacospongia mycofijiensis

et al. 2018

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“…A thietane is obtained in mixture with other products by reaction of a c-unsaturated thiol with bromine (Scheme 3.145). Utilization of the corresponding disulfide allowed exclusive formation of the expected thietane [262]. …”

Section: Formation From Other 3-functionalized Thiol Derivatives A-brmentioning

confidence: 99%

Four‐Membered Heterocycles: Structure and Reactivity

Rousseau

Robin

2011

Modern Heterocyclic Chemistry

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“…An example of the formation of a thietane by this method has, however, been reported in the literature. Mellor et al69 studied the reaction of bromine with the γ‐unsaturated thiol 208 , possessing an amino group α to the olefin. The four‐membered thioether 209 was formed as a mixture with the two thiophene derivatives 210 and 211 .…”

Section: Preparation Of Thietanesmentioning

confidence: 99%