An Easy Access to 4,5-Disubstituted Thiazoles via Base-Induced Click Reaction of Active Methylene Isocyanides with Methyl Dithiocarboxylates

Lingaraju, Gejjalagere S.; Swaroop, Toreshettahally R.; Vinayaka, A. C.; Kumar, Kothanahally S. Sharath; Sadashiva, M. P.; Rangappa, Kanchugarakoppal S.

doi:10.1055/s-0031-1290762

Cited by 61 publications

(5 citation statements)

References 10 publications

(13 reference statements)

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“…In 2012, Rangappa and co‐workers [76] reported an effective synthesis of 4,5‐disubstituted thiazoles 83 using methyl arenes and het ‐arenecarbodithioates 82 through base‐promoted cyclization of active methylene isocyanides 55 (Scheme 45). Several benzodithioates and hetarenecarbodithioates with electron‐deficient and electron‐donating substituents were consistent with cyclization to deliver the desired product in good yields.…”

Section: Synthesis Of Thiazolesmentioning

confidence: 99%

Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles

Kant,

Patel,

Banerjee

et al. 2023

ChemistrySelect

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Nitrogen‐containing heterocycles such as imidazoles, thiazoles, and oxazoles play a significant role in the fields of biological and pharmaceutical chemistry. These compounds were widely used for agrochemical, pesticide, medicinal, and industrial applications. Due to the wide spectrum of structural diversity as well as the biological and pharmaceutical activity of N‐heterocycles, a plethora of reports on their synthesis have appeared in the last few decades. However, developments in various bond‐forming strategies such as C−C, C−N, C−O, C−S, and N−N, as well as C−H activation, have been used as a powerful synthetic tool to derive copious N‐heterocycles. The most prominent and fascinating reports on the synthesis of imidazole, thiazole, oxazoles, and benzimidazole moieties by C−C and C−N coupling reactions, multi‐component and cycloaddition reactions, C−H activation, etc. are discussed in this study. These studies demonstrated the enormous potential of such methods for accelerating modern chemical synthesis and establishing molecular beauty through bonding. The various aspects of the methodologies, like optimized conditions, substrate scope, and mechanistic investigations, are discussed in detail.

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Section: Synthesis Of Thiazolesmentioning

confidence: 99%

Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles

Kant,

Patel,

Banerjee

et al. 2023

ChemistrySelect

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“…Our on-going research work aims at the construction of biologically significant small heterocyclic molecules. , We desire to explore the alternative approaches that can overcome the limitations which are described earlier for the synthesis of 1,3,4-thiadiazoles and 1,3,4-oxadiazoles. Here, we developed operationally simplistic and novel methods with diversified substituents via dehydrative and desulfurative condensation reactions using novel alkyl 2-(methylthio)-2-thioxoacetate and alkyl 2-amino-2-thioxoacetate intermediates.…”

Section: Introductionmentioning

confidence: 99%

Regioselective Synthesis of 2,5-Disubstituted-1,3,4-thiadiazoles and 1,3,4-Oxadiazoles via Alkyl 2-(Methylthio)-2-thioxoacetates and Alkyl 2-Amino-2-thioxoacetates

Santhosh,

Singh,

Sheela

et al. 2023

J. Org. Chem.

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An acid-catalyzed regioselective cyclization reaction of 2,5-disubstituted-1,3,4-thiadiazoles and 1,3,4-oxadiazoles has been developed. The synthetic precursors alkyl 2-(methylthio)-2-thioxoacetates/alkyl 2-amino-2-thioxoacetates react efficiently with acyl hydrazides, which transformed into a series of dehydrative and desulfurative products with employment of p-TSA and AcOH through a regioselective cyclization process. The alkyl 2-amino-2-thioxoacetate pathway generates excellent yield among the mentioned procedures. The reported methods are operationally simplistic and highly efficient with metal-free conditions and demonstrate significant functional group compatibility. Regioselective cyclized products were confirmed by single-crystal X-ray diffraction studies.

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“…Our continuing efforts and interests in developing multi component reactions for the synthesis of various heterocycles [40][41][42][43][44] prompted us to investigate the simple approach to produce structurally diversified threesubstituted indole derivatives through adaptable one-pot multicomponent reactions. Here, we report an experimentally simple and high yielding protocol for the synthesis of 3-indole propanoates/propanoic acid/ propanamide derivatives via one-pot operation.…”

Section: Introductionmentioning

confidence: 99%

Catalyst free sequential one‐pot reaction for the synthesis of 3‐indole propanoates/propanoic acid/propanamides as antituberculosis agents

Rajeev

Kumar

Bommegowda

et al. 2020

J Chinese Chemical Soc

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A highly efficient catalyst free one pot four component synthesis of highly functionalized three‐substituted indole derivatives has been reported. Thus, sequential catalyst free condensation of readily available aldehydes with Meldrum's acid followed by Michael addition of indole resulting three carbon component condensed product and concurrent decarboxylation by the nucleophilic attack of ethanol/water/amines affords three‐indole propanoates/propanoic acid/propanamides in affordable yields. Further, synthesized compounds and standard drugs were evaluated against Mycobacterium tuberculosis H37Rv strain by Alamar blue assay method. Majority of the compounds exhibited the superior activity and specifically compound 4d has MIC 1.6 μg/ml, which is better than the reference drugs used.

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An Easy Access to 4,5-Disubstituted Thiazoles via Base-Induced Click Reaction of Active Methylene Isocyanides with Methyl Dithiocarboxylates

Cited by 61 publications

References 10 publications

Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles

Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles

Regioselective Synthesis of 2,5-Disubstituted-1,3,4-thiadiazoles and 1,3,4-Oxadiazoles via Alkyl 2-(Methylthio)-2-thioxoacetates and Alkyl 2-Amino-2-thioxoacetates

Catalyst free sequential one‐pot reaction for the synthesis of 3‐indole propanoates/propanoic acid/propanamides as antituberculosis agents

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