One-pot synthesis of functionalized thioureas by reaction of benzoyl isothiocyanates, secondary amines, and alkyl propiolates

Yavari, Issa; Sayyed-Alangi, S. Zahra; Sabbaghan, Maryam; Hajinasiri, Rahimeh; Iravani, Nasir

doi:10.1007/s00706-008-0899-z

Cited by 16 publications

(12 citation statements)

References 12 publications

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“…A multicomponent reaction of benzoyl isothiocyanates 125, alkyl propiolates 126, secondary amines 127, and Ph 3 P leading to an efficient synthesis of functionalized thioureas has been reported. 85 Addition of Ph 3 P to various activated alkynes like dibenzoylacetylene, dicyanoacetylene, or dimethylacetylenedicarboxylate (DMAD) generating zwitterionic intermediate was reported as early as 1961 by Tebby and coworkers. 86 Initially a 1,3-dipolar intermediate 130 was formed from Ph 3 P and the acetylenic ester, which was subsequently protonated by the benzoyl thiourea 129, formed from addition of amine 127 to aroyl isothiocyanates 125.…”

Section: Multicomponent Reactions Of Acyl Isothiocyanatesmentioning

confidence: 99%

Reactivity and diverse synthetic applications of acyl isothiocyanates

Bedane¹,

Singh²

2015

Arkivoc

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Isothiocyanates constitute a group of heterocumulenes containing N=C=S functionality that is of immense importance in organic synthesis. The presence of carbonyl group in acyl isothiocyanates imparts unique reactivity to acyl isothiocyanates. The chemistry of acyl isothiocyanates, in particular, is very rich and diverse, and has been employed in synthesis of a number of biologically important heterocycles. This review article discusses the acyl isothiocyanate chemistry leading to the synthesis of biologically important heterocyclic skeletons. These include highly functionalized thiazoles, thiadiazoles, triazoles, benzimidazoles, dithiolane, spiro-fused oxazolines, triazines, and oxazines, etc. The role of acyl isothiocyanates as acylating agent and thiocyanate transfer reagent is also discussed.

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Section: Multicomponent Reactions Of Acyl Isothiocyanatesmentioning

confidence: 99%

Reactivity and diverse synthetic applications of acyl isothiocyanates

Bedane¹,

Singh²

2015

Arkivoc

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“…However, in spite of their potential utility, many of these methods suffer from drawbacks, such as harsh reaction conditions, cumbersome product isolation procedures, and expensive catalysts. As a part of our current studies, on the synthesis of sulfur-containing organic compounds (21,22), in this article, we describe an efficient method for the synthesis of functionalized 2,3-dihydrothiazoles under solvent-free conditions. This catalyst-free and one-pot synthetic method is facile with an easy workup procedure that gives pure target compounds containing several potential centers for further modification.…”

Section: Introductionmentioning

confidence: 99%

Solvent-free synthesis of 1-[3-alkyl-4-methyl-2-thioxo-2,3-dihydrothiazole-5-yl]-ethanones in a multicomponent reaction

Iravani

Karami

Asadimoghaddam

et al. 2012

Journal of Sulfur Chemistry

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A simple and efficient one-pot synthesis of 1-[3-alkyl-4-methyl-2-thioxo-2,3-dihydrothiazole-5-yl]-ethanones from the reaction of primary alkylamines and carbon disulfide in the presence of 3-chloro acetylacetone is described. This protocol has several advantages such as lack of need for a solvent and catalyst, high yields, mild conditions and short reaction times. R N H 2 H 3 C O O CH 3 Cl + r.t. , 2-4 hr CS 2 solvent-free N S S R CH 3 O CH 3

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“…As a part of our current studies, on the synthesis of sulfur-containing organic compounds, [25][26][27][28][29][30] in this article, we wish to report an efficient and convenient synthetic method for the synthesis of alkyl-2-(alkylimino)-4-methyl-3-phenyl-2,3-dihydrothiazole-5-carboxylate and dialkyl 3,3¢-(1,4-phenylene)-bis-[2-(alkylimino)-4-methyl-2,3-dihydrothiazole-5-carboxylate] derivatives under solventand catalyst-free conditions. This one-pot synthetic method is facile with an easy workup procedure that gives pure target compounds containing several potential centers for further modification.…”

Section: Introductionmentioning

confidence: 99%

ChemInform Abstract: Three‐Component One‐Pot Synthetic Route to Functionalized N‐Phenyl‐ and N,N‐(1,4‐Phenylene)‐2‐alkylimino‐2,3‐dihydrothiazoles under Mild, Solvent‐ and Catalyst‐Free Conditions.

et al. 2014

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A simple and efficient one‐pot synthesis of alkyl‐2‐(alkylimino)‐4‐methyl‐3‐phenyl‐2,3‐dihydrothiazole‐5‐carboxylate and dialkyl 3,3′‐(1,4‐phenylene)‐bis‐[2‐(alkylimino)‐4‐methyl‐2,3‐dihydrothiazole‐5‐carboxylate] derivatives from the reaction of phenylisothiocyanate (and also 1,4‐phenylene diisothiocyanate) and primary alkylamines in the presence of 2‐chloro‐1,3‐dicarbonyl compounds is described. This new protocol has several advantages such as lack of necessity of the catalyst and solvent, good yields,mild conditions and short times for reaction.

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One-pot synthesis of functionalized thioureas by reaction of benzoyl isothiocyanates, secondary amines, and alkyl propiolates

Cited by 16 publications

References 12 publications

Reactivity and diverse synthetic applications of acyl isothiocyanates

Reactivity and diverse synthetic applications of acyl isothiocyanates

Solvent-free synthesis of 1-[3-alkyl-4-methyl-2-thioxo-2,3-dihydrothiazole-5-yl]-ethanones in a multicomponent reaction

ChemInform Abstract: Three‐Component One‐Pot Synthetic Route to Functionalized N‐Phenyl‐ and N,N‐(1,4‐Phenylene)‐2‐alkylimino‐2,3‐dihydrothiazoles under Mild, Solvent‐ and Catalyst‐Free Conditions.

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