Efficient synthesis of 2-thioxo-1,3-thiazolanes from primary amines, CS2, and ethyl bromopyruvate

Yavari, Issa; Seyfi, Samereh; Hossaini, Zinatossadat; Sabbaghan, Maryam; Shirgahi‐Talari, Faezeh

doi:10.1007/s00706-008-0953-x

Cited by 44 publications

(13 citation statements)

References 19 publications

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“…In this three-component method, phenylthiosemicarbazide reacts smoothly with dimethylacetylenedicarboxylate in the presence of aldehydes or ketones under solvent-free conditions to produce thiazolidine-4-ones as indicated in Scheme 9.18. An efficient solvent-less green synthesis of 2-thioxo-1,3-thiazolanes 37 and ethyl 3-alkyl-4-oxo-2-thioxo-1,3-thiazolane-5-carboxylates 38 as new TZD-based heterocycle via reaction of primary amines with CS 2 in the presence of ethyl bromopyruvate 34 and diethyl 2-chloromalonate 35 was reported by Yavari et al [39,40]. These new multicomponent reactions were done in a green method in which the yields of biologically interesting structure are typically 90 %.…”

Section: Green Synthesis Of Rhodanines and Tzdsmentioning

confidence: 94%

Synthesis and Synthetic Applications of Biologically Interesting Rhodanine and Rhodanine-Based Scaffolds

Rostamnia

Doustkhah

2014

Green Chemistry: Synthesis of Bioactive Heterocycles

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Rhodanine and thiazolidinone (TZD) heterocycles are attractive targets in organic and medicinal chemistry owing to their potency in a wide spectrum of biological activities and can also serve as synthetic intermediates for many kinds of pharmaceuticals or drug precursors. Consequently, looking for efficient and concise green methods for the synthesis of these types of compounds is a major challenge in chemistry. As a result, many green methods have been used to synthesize structurally complex and diverse rhodanine and TZDs in recent years. The purpose of this chapter is to discuss the recent green synthesis of the rhodanine and TZD heterocyclic scaffolds including aqueous medium synthesis, ionic liquid, microwave, ultrasonic irradiation, solvent-free methods, solid catalysts, such as mesoporous, magnetic nanoparticles, etc.

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Section: Green Synthesis Of Rhodanines and Tzdsmentioning

confidence: 94%

Synthesis and Synthetic Applications of Biologically Interesting Rhodanine and Rhodanine-Based Scaffolds

Rostamnia

Doustkhah

2014

Green Chemistry: Synthesis of Bioactive Heterocycles

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“…Gold‐catalyzed functionalization reactions, and multicomponent reactions based on amine and CS 2 are of examples of this approach in the organic synthesis. This method is used for the synthesis of complex compounds, including dialkylaminocarbothioyl thioureas, naphthoquinon‐1,3‐dithioles, 2‐thioxo‐1,3‐thiazolanes, 4‐oxo‐2‐thioxo‐1,3‐thiazinanes, 2‐thioxo‐2,3‐dihydroquinazolin‐4(1 H )‐one, and stable ionic liquids . Regarding the applicability of nucleophilic substitution reactions on benzene on the one hand, and multicomponent reactions based on amine and carbon disulfide on the other hand; in this article, we develop a novel method based on multicomponent reactions of amine and carbon disulfide including fluoronitrobenzene for the synthesis of 4‐nitrophenyl methylcarbamodithioate derivatives (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Multicomponent reaction of amine, carbon disulfide, and fluoronitrobenzene via nucleophilic attack on the fluorinated carbon for the synthesis of nitrophenyl methylcarbamodithioates

Bahadorikhalili

Mohammadi

Asadi

et al. 2019

J Chinese Chemical Soc

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In this paper, multicomponent reaction of amine, carbon disulfide and fluoronitrobenzene is reported for the synthesis of nitrophenyl methylcarbamodithioate derivatives. The method is based on the nucleophilic attack of the activated methylcarbamodithioate salt to fluoronitrobenzene. Several starting materials are tested and successfully produced the corresponding nitrophenyl methylcarbamodithioate. A possible mechanism for the reaction is suggested. K E Y W O R D S amine-CS 2 reaction, aromatic nucleophilic substitution, multicomponent reaction, nitrophenyl methylcarbamodithioate White solid; yield: 85%, mp = 210-215 C. IR (KBr): 3,053 (C-H aromatic ), 1,610 (C=S) cm −1 ; 1 H NMR (DMSO-d6, 500 MHz): δ = 3.87 (s, 3H, O-CH 3 ), 4.10 (m, 4H, N-CH 2-piperazine ), 4.51 (m, 4H, N-CH 2-piperazine ), 6.93 (d, J = 7.0 Hz, 1H, H 3 0 ), 7.03 (d, J = 7.5 Hz, 1H, H 6 0), 7.43 (t, J = 7.5 Hz, 1H, H 5 0 ), 7.57 (t, J = 7.0 Hz, 2H, H 4 0 ), 7.86 (d, J = 7.5 Hz, 2H, H 2,6 ), and 8.01 (d, J = 7.5 Hz, 2H, H 3,5 ) ppm; 13 C NMR (DMSO-d6, 125 MHz): δ = 50.2, 51.9, S C H E M E 2 Suggested mechanism for the synthesis of nitrophenyl methylcarbamodithioate derivatives White solid; yield: 75%, mp =203-205 C. IR (KBr): 3,062 (C-H aromatic ), 1,610 (C=S) cm −1 ; 1 H NMR (DMSO-d6, 500 MHz): δ = 4.09 (m, 4H, N-CH 2-piperazine ), 4.46 (m, 4H, N-CH 2-piperazine ), 6.84-6.99 (m, 5H, Ph), 7.43 (t, J = 7.5 Hz, 1H, H 5 ), 7.57 (t, J = 7.0 Hz, 2H, H 4 ), 7.85 (d, J = 7.5 Hz, 2H, H 6 ), and 8.01 (d, J = 7.5 Hz, 2H, H 3 ) ppm; 13 C NMR (DMSO-d6, 125 MHz): δ = 49. 9, 52.9, 115.7, 115.9, 118.4, 120.5, 128.9, 133.0, 133.4, 141.1, 141.5, 147.7, and 195.2 ppm; MS (70 eV): m/z = 359 (M+). 3.3.7 | 2-Nitrophenyl 4-(p-tolyl)piperazine-1-carbodithioate (4g) White solid; yield: 75%, mp =236-240 C. IR (KBr): 3,037 (C-H aromatic ), 1,608 (C=S) cm −1 ; 1 H NMR (DMSO-d6, 500 MHz): δ = 2.27 (s, 3H, CH 3 ), 4.07 (m, 4H, N-CH 2-piperazine ), 4.46 (m, 4H, N-CH 2-piperazine ), 6.81 (d, J = 8.0 Hz, 2H, H 3 0 ,5 0 ), 7.09 (d, J = 8.0 Hz, 2H, H 2 0 ,6 0 ), 7.43 (t, J = 7.5 Hz, 1H, H 5 ), 7.56 (t, J = 7.0 Hz, 2H, H 4 ), 7.85 (d, J = 7.5 Hz, 2H, H 6 ), and 8.01 (d, J = 7.5 Hz, 2H, H 3 ). ppm; 13 C NMR (DMSO-d6, 125 MHz): δ = 20.196.3 ppm; MS (70 eV): m/z = 373 (M+). 3.3.8 | 2-Nitrophenyl 4-benzylpiperazine-1-carbodithioate (4h)

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“…This method is well reviewed and showed an appropriate method for the synthesis of a wide variety of organic compounds . The reactions with carbadiimides, quinones, fluoronitrobenzene, and ethyl bromopyruvate are only a number of the reported reactions, showing the significance of amine‐CS 2 approach in the synthesis of complex organic compounds.…”

Section: Introductionmentioning

confidence: 99%

Amine‐carbon disulfide promoted synthesis of novel benzo[e][1,3]thiazepin‐5(1H)‐one derivatives

Asgari

Bahadorikhalili

Asadi

et al. 2019

Journal of Heterocyclic Chem

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In this paper, a simple method is introduced for the synthesis of novel 4-substituted-3-thioxo-3,4-dihydrobenzo[e][1,3]thiazepin-5(1H)-one derivatives. The synthesis is based on a two-step reaction of 2-methylbenzoic acid, an amine, and carbon disulfide. In the first step, 2-methylbenzoic acid reacts with sulfuric acid in ethanol, followed by the reaction with N-bromosuccinimide to produce ethyl 2-(bromomethyl)benzoate. Amine and carbon disulfide react in a separate flask in basic medium to give carbamodithioate salt. Carbamodithioate and ethyl 2-(bromomethyl)benzoate react together in dimethylformamide to produce the desired 4-substituted-3-thioxo-3,4-dihydrobenzo[e][1,3]thiazepin-5(1H)-one derivatives. The method is simple and fast and is applicable to a wide variety of substrates and gives the desired products in high isolated yields.

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Efficient synthesis of 2-thioxo-1,3-thiazolanes from primary amines, CS2, and ethyl bromopyruvate

Cited by 44 publications

References 19 publications

Synthesis and Synthetic Applications of Biologically Interesting Rhodanine and Rhodanine-Based Scaffolds

Synthesis and Synthetic Applications of Biologically Interesting Rhodanine and Rhodanine-Based Scaffolds

Multicomponent reaction of amine, carbon disulfide, and fluoronitrobenzene via nucleophilic attack on the fluorinated carbon for the synthesis of nitrophenyl methylcarbamodithioates

Amine‐carbon disulfide promoted synthesis of novel benzo[e][1,3]thiazepin‐5(1H)‐one derivatives

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