Synthesis of 6-Membered-Ring Fused Thiazine-Dicarboxylates and Thiazole-Pyrimidines via One-Pot Three-Component Reactions

Mohlala, Reagan Lehlogonolo; Coyanis, E. Mabel; Fish, Muhammad Qasim; Fernandes, Manuel A.; Bode, Moira L.

doi:10.3390/molecules26185493

Cited by 7 publications

(3 citation statements)

References 53 publications

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“…The reaction to achieve the products was done through visible light using 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) as an additive under mild conditions. The 3CR of 3-amino-1,2,4-triazole (a), aldehyde (b), and ethyl cyanoacetate (c) gave rise to dihydro- [1,2,4]triazolo [1,5-a]pyrimidines (23) under green chemical production using poly-melamineformaldehyde (mPMF) as catalyst (Scheme 21) [37]. The reactions were performed at room temperature under solvent-free conditions.…”

Section: Green Chemistrymentioning

confidence: 99%

“…Figure 1, represents the overall practical idea of linear synthesis compared to MCRs, which depict at least four separate reactants (building blocks) coming together to generate a single product. MCRs are viewed as a practical strategy in synthetic chemistry and offer several advantages over conventional one-or two-component reactions by minimising the number of sequential multiple reactions necessary and frequently resulting in better yields [4,5,6]. The use of MCRs in organic synthesis towards medicinal chemistry, drug discovery, green chemistry, polymerisation and other related applications remains one of the better alternative routes for the synthesis and preparation of desired products.…”

Section: Introductionmentioning

confidence: 99%

“…Scheme 24. 4CR for the synthesis of 1,2,4-triazole-tagged 1,4-dihydropyridine derivatives.Ma and associates[41] reported the green chemical diastereoselective synthesis of tetrahydropyrrolo[1,2-d][1,4]benzodiazepines(26) and tetrahydropyrrolo[1,2-d][1,4]diazepinones(27), as shown in Scheme 25. The 4CR of L-alanine ethyl ester hydrochloride (a) with N-ethylmaleimide (b), and 2-azidobenzaldehyde (c) in the presence of phenacyl bromide or phenylglyoxylic acid using acetonitrile as a solvent under microwave gave good yields.…”

mentioning

confidence: 99%

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Multicomponent Reactions as an Efficient and Facile Alternative Route in Organic Synthesis and Applications

Mohlala¹,

Rashamuse²,

Coyanis³

2023

Preprint

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Multicomponent reactions (MCRs) have been used for more than a century; since their discovery in 1850 by Strecker. To date, MCRs route is regarded as a beneficial strategy due to its capacity to quickly produce molecular diversity and structural complexity of interest for a variety of applications. Despite having famous MRCs such as the Ugi, Passerini, Biginelli, and Hantzsch, this re-view portrays the importance of MCRs in the synthesis of desired products towards applications such as medicinal purposes, sustainable chemistry, and polymerisation. MCRs provide ad-vantages such as reducing the number of sequential multiple reactions to one step, atom economy, recyclable catalysts, mild conditions, preventing waste and reduce solvent use.

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Section: Green Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Multicomponent Reactions as an Efficient and Facile Alternative Route in Organic Synthesis and Applications

Mohlala¹,

Rashamuse²,

Coyanis³

2023

Preprint

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Novel 1,4 benzothiazine 3-one derivatives as anticonvulsant agents: Design, synthesis, biological evaluation and computational studies

Ataollahi

Solhjoo

Rezaei

et al. 2023

Computational Biology and Chemistry

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A facile and efficient one-pot 3-component reaction (3-CR) method for the synthesis of thiazine-based heterocyclic compounds using zwitterion adduct intermediates

Mohlala,

Coyanis

2024

Physical Sciences Reviews

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Multicomponent reactions (MCRs) are considered a green strategy by generating diversity of scaffolds from less synthetic effort and safe conditions. This work present the synthesis of dimethyl 8-(tert-butylamino)-4-oxo-4,6-dihydropyrimido[2,1-b][1,3]thiazine-6,7-dicarboxylate in low to moderate yields 33–74 % from the prepared 2-amino-4H-1,3-thiazin-4-one derivatives containing both an acidic proton and a suitable nucleophile with alkyl isocyanides and DMAD/DEtAD. The work portrays facile method under green chemical production processes using green solvents such as acetone, ethanol, isopropanol, and 2-methyl-tetrahydrofuran. This chapter shows the flexibility of zwitterion adduct from the reaction of alkyl isocyanide and DMAD. The zwitterion adduct is trapped by 2-amino-4H-1,3-thiazin-4-one derivatives and forms fused [6-6] heterocyclic compounds. The preparation of starting material thiazine was carried out at different condition from 0 °C temperatures to reflux, while the synthesis of novel dimethyl 8-(tert-butylamino)-4-oxo-4,6-dihydropyrimido[2,1-b][1,3]thiazine-6,7-dicarboxylates was done at room temperature without the use of catalyst.

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Synthesis of 6-Membered-Ring Fused Thiazine-Dicarboxylates and Thiazole-Pyrimidines via One-Pot Three-Component Reactions

Cited by 7 publications

References 53 publications

Multicomponent Reactions as an Efficient and Facile Alternative Route in Organic Synthesis and Applications

Multicomponent Reactions as an Efficient and Facile Alternative Route in Organic Synthesis and Applications

Novel 1,4 benzothiazine 3-one derivatives as anticonvulsant agents: Design, synthesis, biological evaluation and computational studies

A facile and efficient one-pot 3-component reaction (3-CR) method for the synthesis of thiazine-based heterocyclic compounds using zwitterion adduct intermediates

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