Investigation of the Reaction of <i>In Situ</i> Prepared Dithiocarbamic Acids with Itaconic Anhydride in Water

Halimehjani, Azim Ziyaei; Nosood, Yazdanbakhsh Lotfi

doi:10.1002/jhet.2957

Cited by 3 publications

(3 citation statements)

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“…The addition of the carbenoid-C atom of the isocyanides onto the iminium group followed by the addition of the carboxylate ion onto the C -atom of the nitrilium ion leads to the formation of the adduct 178, which underwent intramolecular acylation (Mumm rearrangement) [77] to give 175 (Scheme 50). Similarly, one-pot three-component reaction of primary amines (RNH2), carbon disulfide (CS2) and itaconic anhydride (173) in water resulted in the formation of 2-(3-alkyl-4-oxo-2-thioxo-1,3-thiazinan-5-yl) acetic acid derivatives 174a-i in 68%-95% yields (Scheme 51) [78]. Similarly, one-pot three-component reaction of primary amines (RNH2), carbon disulfide (CS2) and itaconic anhydride (173) in water resulted in the formation of 2-(3-alkyl-4-oxo-2-thioxo-1,3-thiazinan-5-yl) acetic acid derivatives 174a-i in 68%-95% yields (Scheme 51) [78].…”

Section: Synthesis Of 13-thiazinane-2-thione-4-one Derivativesmentioning

confidence: 99%

“…Similarly, one-pot three-component reaction of primary amines (RNH2), carbon disulfide (CS2) and itaconic anhydride (173) in water resulted in the formation of 2-(3-alkyl-4-oxo-2-thioxo-1,3-thiazinan-5-yl) acetic acid derivatives 174a-i in 68%-95% yields (Scheme 51) [78]. Similarly, one-pot three-component reaction of primary amines (RNH2), carbon disulfide (CS2) and itaconic anhydride (173) in water resulted in the formation of 2-(3-alkyl-4-oxo-2-thioxo-1,3-thiazinan-5-yl) acetic acid derivatives 174a-i in 68%-95% yields (Scheme 51) [78]. Solvent-free one-pot stereoselective synthesis of 1,3-thiazinane-2-thione derivatives 186 (85-89%) was achieved through the interaction between primary amines, carbon disulfide and α,β-unsaturated aldehydes (Scheme 56) [81].…”

Section: Synthesis Of 13-thiazinane-2-thione-4-one Derivativesmentioning

confidence: 99%

“…Scheme 50. The mechanism for the formation of 4-oxo-2-thioxo-1,3-thiazinane 175.Similarly, one-pot three-component reaction of primary amines (RNH 2 ), carbon disulfide (CS 2 ) and itaconic anhydride (173) in water resulted in the formation of 2-(3-alkyl-4-oxo-2-thioxo-1,3-thiazinan-5-yl) acetic acid derivatives 174a-i in 68-95% yields (Scheme 51)[78].…”

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Chemistry of Substituted Thiazinanes and Their Derivatives

et al. 2020

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Thiazinanes and its isomeric forms represent one of the most important heterocyclic compounds, and their derivatives represented a highly potent drug in disease treatment such as, 1,1-dioxido-1,2-thiazinan-1,6-naphthyridine, which has been shown to have anti-HIV activity by a mechanism that should work as anti-AIDS treatment, while (Z)-methyl 3-(naphthalen-1-ylimino)- 2-thia-4-azaspiro[5 5]undecane-4-carbodithioate showed analgesic activity, cephradine was used as antibiotic and chlormezanone was utilized as anticoagulants. All publications were interested in the chemistry of thiazine (partially or fully unsaturated heterocyclic six-membered ring containing nitrogen and sulfur), but no one was dealing with thiazinane itself which encouraged us to shed new light on these interesting heterocycles. This review was focused on the synthetic approaches of thiazinane derivatives and their chemical reactivity.

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Section: Synthesis Of 13-thiazinane-2-thione-4-one Derivativesmentioning

confidence: 99%