Convenient and simple synthesis of 2-aminothiazoles by the reaction of α-halo ketone carbonyls with ammonium thiocyanate in the presence of N-methylimidazole

Meshram, H. M.; Thakur, Pramod B.; Babu, B. Madhu; Bangade, Vikas M.

doi:10.1016/j.tetlet.2012.07.080

Cited by 25 publications

(8 citation statements)

References 53 publications

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“…Retrosynthetic analysis (Fig. 2) shows that the target molecules can be obtained by a two-step route (A) through intermediate 2-amino-1,3-thiazole-4-acetic acid esters 5, which have been reported earlier in the literature [5,6,12]. A similar method has been reported, where morpholine derivatives of 1,3-thiazole were synthesized and found to function as ion channel modulators [15].…”

Section: Introductionmentioning

confidence: 69%

“…Arylamides from 2-amino-1,3-thiazoles have been reported as antiviral agents [11]. The introduction of a phenoxypropanolamine side chain in 2-amino-1,3-thiazole-4-acetic acid has resulted in selective β3-adrenergic receptor agonists [12]. 2-Amino-1,3-thiazole with a methoxyimino function at C-4 forms part of cefotaxime [13].…”

Section: Introductionmentioning

confidence: 99%

“…It is also pertinent to mention that the amides reported in the literature were prepared by the two-step route [12] involving the synthesis of thiazole esters or acids 5 followed by amidation. In the present paper, we describe a single-step synthesis of 4-arylacetamido-2-amino-1,3-thiazoles by the reaction of ω-bromoacetoacetanilide and thioureas through route B (Fig.…”

Section: Introductionmentioning

confidence: 99%

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A new route for the synthesis of 4-arylacetamido-2-aminothiazoles and their biological evaluation

Madhura

Revankar

Kulkarni

2015

Zeitschrift Für Naturforschung B

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A series of 4-arylacetamido-2-amino-and 2-arylamino-1,3-thiazoles (4a-o) were synthesized in a single step in high yields from ω-bromoacetoacetanilides and thiourea/phenyl thioureas and were characterized by spectral and analytical methods. The compounds were evaluated for their in vitro antibacterial antifungal and antioxidant activities. In vitro antimicrobial evaluation of these compounds indicated their specificity towards Gram-positive species. p-Tolyl and m-chlorophenyl substituents on the arylamino moiety (compounds 4b and 4g) exhibited the lowest minimum inhibitory concentration values. The other compounds exhibited promising antimicrobial and moderate antioxidant activity.

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Section: Introductionmentioning

confidence: 69%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A new route for the synthesis of 4-arylacetamido-2-aminothiazoles and their biological evaluation

Madhura

Revankar

Kulkarni

2015

Zeitschrift Für Naturforschung B

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“…Meshram et al . developed a synthetic protocol for the preparation of substituted 2‐aminothiazoles ( 228 ) using N ‐methyl imidazole as a catalyst.…”

Section: Synthesis Of Thiazolesmentioning

confidence: 99%

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

et al. 2020

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Thiazole frame work represents a vital pharmacophore in several areas of chemistry. Consequently, several synthetic protocols to construct and functionalize this core, in an attempt to generate diverse thiazole containing architectures have been developed by various researchers across the globe. These wide range of methodologies developed will allow the access to fully decorated thiazole containing new chemical entities that can find various application in the field of medicinal chemistry, agrochemicals and material science. This review will provide an insight in to the various synthons used in construction and diversification of this core. Diversely functionalized thiazole analogs are considered as a vital azole framework present in many natural products. This prominent heterocycle also constitutes an important pharmacophore in medicinal chemistry, in agrochemicals and in molecules for material science applications. All these above‐mentioned features of thiazole necessitates the continuous development of efficient methods to access this heterocycle. Accordingly, various researchers across the globe have come up with efficient synthetic protocols in an attempt functionalize different positions of this important scaffold. This review aims at highlighting some of the latest synthetic approaches to di/tri‐substituted thiazole analogs which are known to possess a wide spectrum of biological activities.

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“…Recently, Meshram et al . have reported the synthesis of 2‐aminothiazoles by the reaction of α‐haloketone carbonyls with ammonium thiocyanate in the presence of N ‐methylimidazole . Despite these procedures, novel and widely applicable green methodologies for the synthesis of 2‐aminothiazole derivatives are still in demand.…”

Section: Introductionmentioning

confidence: 99%

18‐Crown‐6 Catalyzed Microwave‐mediated Synthesis of Symmetric Bis‐Heterocyclic Compounds under Solvent‐free Condition

Rathnasamy¹,

Prabakaran

Murugesan

et al. 2014

Journal of Heterocyclic Chem

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An efficient, solvent‐free and 18‐crown‐6 catalyzed method for the synthesis of N‐alkyl‐4‐(4‐(5‐(2‐(alkyl‐amino)thiazol‐4‐yl)pyridin‐3‐yl)phenyl)thiazol‐2‐amine, N‐alkyl‐4‐(5‐(2‐alkyamino)thiazol‐4‐yl)pyridine‐3‐yl)thiazol‐2‐amine, and 4,4′‐bis‐{2‐[amino]‐4‐thiazolyl}biphenyl bis‐heterocyclic derivatives via microwave accelerated cyclization is presented.

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Convenient and simple synthesis of 2-aminothiazoles by the reaction of α-halo ketone carbonyls with ammonium thiocyanate in the presence of N-methylimidazole

Cited by 25 publications

References 53 publications

A new route for the synthesis of 4-arylacetamido-2-aminothiazoles and their biological evaluation

A new route for the synthesis of 4-arylacetamido-2-aminothiazoles and their biological evaluation

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

18‐Crown‐6 Catalyzed Microwave‐mediated Synthesis of Symmetric Bis‐Heterocyclic Compounds under Solvent‐free Condition

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