Cobalt mediated by desulfurization toward the synthesis of isothiocyanates

Seelam, Mohan; Shaik, Bajivali; Kammela, Prasada Rao

doi:10.1080/00397911.2016.1224351

Cited by 24 publications

(13 citation statements)

References 14 publications

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“…Isothiocyanates are interesting molecules that are naturally produced from the hydrolysis of glucosinolates. 2 They can be synthesized many different ways, including through the decomposition of dithiocarbamate salts, 5,8,11,[13][14][15][16][17][18][19][20][21] from hydroximoyl chlorides, 24 using elemental sulfur, 25 via microwave-assisted methods, 26 or by the tandem Staudinger/aza-Wittig reactions. 27,28 Eleven different desulfurization methods were discussed in this short review.…”

Section: Resultsmentioning

confidence: 99%

“…Most of the time, this dithiocarbamate salt is isolated prior to desulfurization. There are many available desulfurization methods; this review will focus on the use of 11 different agents, namely thiophosgene, 11 triphosgene, 13 claycop, 14 hydrogen peroxide, 15 iodine, 16 lead nitrate, 17 ethyl chloroformate, 18 cobalt(II) chloride, 19 copper(II) sulfate, 20 sodium persulfate, 5 and tosyl chloride. 21 These reagents are summarized in Table 1.…”

Section: Scheme 2 Reaction Of a Primary Amine With Thiophosgene In Thmentioning

confidence: 99%

“…Another method of desulfurization is by using metalbased reagents such as cobalt(II) chloride 19 and copper(II) sulfate. 20 These are both fairly quick methods, achieving the desired result in a matter of hours.…”

Section: Scheme 8 Ethyl Chloroformate As Desulfurization Agent 18mentioning

confidence: 99%

“…These methods are useful in that the catalysts are cheap, readily available, and stable in air. 19,20 These reactions can be performed under mild conditions, such as the use of room temperature. There are also no by-products to these reactions, which makes workup and purification much simpler 19,20 (Scheme 9).…”

Section: Scheme 8 Ethyl Chloroformate As Desulfurization Agent 18mentioning

confidence: 99%

“…Summary of Desulfurization Agents5,8,11,[13][14][15][16][17][18][19][20][21] The use of triphosgene as desulfurization agent13 …”

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confidence: 99%

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Synthesis of Isothiocyanates: An Update

Eschliman¹,

Bossmann

2019

Synthesis

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Isothiocyanates (ICTs) are a group of molecules that can be used for many different purposes, they exhibit anticancer, antimicrobial, antibiotic, and anti-inflammatory properties. The synthesis of isothiocyanates has been a focus of many researchers for nearly the past 100 years. One of the most common synthetic methods is to form a dithiocarbamate salt, either as the first step or in situ, and then treat the salt with a desulfurization agent to reach the isothiocyanate. There are many different desulfurization agents available. Among these, there are eleven in particular that will be discussed in this short review, namely thiophosgene, lead nitrate, ethyl chloroformate, hydrogen peroxide, triphosgene, iodine, cobalt, copper, sodium persulfate, claycop, and tosyl chloride. There are four additional particular methodologies that stand out from the literature available on this topic that will be covered, namely the production of isothiocyanates from hydroximoyl chlorides, via elemental sulfur, microwave-assisted synthesis, and through the tandem Staudinger/aza-Wittig reactions.1 Introduction1.1 Metabolism of Glucosinolates2 Synthesis of Isothiocyanates2.1 Isothiocyanates from the Decomposition of Dithiocarbamate Salts2.2 Isothiocyanates from Hydroximoyl Chlorides2.3 Isothiocyanates Produced via Elemental Sulfur2.4 Microwave-Assisted Synthesis of Isothiocyanates2.5 Isothiocyanates via the Tandem Staudinger/aza-Wittig Reactions3 Conclusion

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Section: Resultsmentioning

confidence: 99%

Section: Scheme 2 Reaction Of a Primary Amine With Thiophosgene In Thmentioning

confidence: 99%

Section: Scheme 8 Ethyl Chloroformate As Desulfurization Agent 18mentioning

confidence: 99%

Section: Scheme 8 Ethyl Chloroformate As Desulfurization Agent 18mentioning

confidence: 99%

“…Summary of Desulfurization Agents5,8,11,[13][14][15][16][17][18][19][20][21] The use of triphosgene as desulfurization agent13 …”

mentioning

confidence: 99%

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Synthesis of Isothiocyanates: An Update

Eschliman¹,

Bossmann

2019

Synthesis

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Efficient Copper‐Promoted Tandem Multi‐Component Strategy: The Synthesis of 1‐ Aryl/Alkyl‐5‐(N‐Benzoylamino) Tetrazoles and Guanidine's

Shaik¹,

Seelam²,

Tamminana

et al. 2017

ChemistrySelect

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Efficient, simple and multi component methodology has been demonstrated for the construction of l‐Aryl/Alkyl‐5‐(N‐Benzoylamino) tetrazoles and guanidine's. These compounds can be used as intermediates for the synthesis of heterocyclic compounds such as substituted 2‐(N‐benzoyl) benzimidazoles and fused cyclic tetrazoles. Target products were obtained from benzyol chloride via in situ consecutive formation of benzoyl isothiocyanates and benzyol aryl thiourea. Moreover, desulphurization was also observed during this methodology. In addition, functional group tolerance and reaction mechanism have also been studied.

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Synthesis of Benzimidazoles via Domino Intra and Intermolecular C‐N Cross‐Coupling Reaction

2018

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The synthesis of aminobenzimidazoles has been demonstrated under mild reaction conditions using cobalt catalyst in one pot reaction. This methodology involved domino intra and intermolecular C-N cross-coupling reaction. In addition, functional group tolerance has been also explored.Benzimidazoles [1][2][3][4][5][6][7][8][9][10] and 2-aminobenzimidazoles [11][12][13][14][15][16][17][18][19][20][21] are very powerful compounds because of their applications in therapeutic [22][23] and biological sciences ( Figure 1). [24][25] These compounds were used as neuropeptide YY1 receptor antagonist, [26] N-methyl-D-aspartate (NMDA) antagonist, [27] factor Xa(FXa) inhibitor, [28] poly(ADP-ribose)polymerase (PARP) inhibitor [29] and non-peptide thrombin inhibitor. [30] In addition, these compounds show anti-inflammatory, antimicrobial and antibacterial activities. [31] Apart from that, these compounds can also be used for the synthesis of dyes and high-temperature resistance polymers. [32] Therefore, the construction of benzimidazole derivatives were developed by many researchers via both traditional methods [33][34][35] and C-N cross-coupling reactions using various transition metals such as Cu, [36][37][38][39][40] Pd, [41][42][43] Co, [44] Zn, [45][46][47] and Ru. [48] In this connection, we would like to demonstrate the methodology for the synthesis of benzimidazoles from thiourea in one pot reaction via desulphurization/substitution/domino C-N cross-coupling reaction using cobalt source as catalyst under mild reaction conditions.

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Cobalt mediated by desulfurization toward the synthesis of isothiocyanates

Cited by 24 publications

References 14 publications

Synthesis of Isothiocyanates: An Update

Synthesis of Isothiocyanates: An Update

Efficient Copper‐Promoted Tandem Multi‐Component Strategy: The Synthesis of 1‐ Aryl/Alkyl‐5‐(N‐Benzoylamino) Tetrazoles and Guanidine's

Synthesis of Benzimidazoles via Domino Intra and Intermolecular C‐N Cross‐Coupling Reaction

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