Triphosgene: An Efficient Catalyst for Synthesis of Isothiocyanates

Chaskar, Atul; Yewale, S.; Bhagat, Ramesh; Langi, Bhushan

doi:10.1080/00397910801997744

Cited by 13 publications

(9 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In order to explore these transformations, the convenient preparation of intermediate heteroaryl‐isothiocyanates 3 is obviously important. Although the substituted isothiocyanate can be prepared by several methods , we desire to develop convenient and effective methods for these heterocyclic isothiocyanates. The representative compound 6‐chloropyridin‐3‐amine was chosen as a substrate for the optimization of the reaction conditions, and four different methods have been fully investigated (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Convenient Structural Diversity‐Guided Synthesis of Functionalized Sulfur‐Containing Heterocycles via α‐Substituted Cyanoacetamides

2016

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

A convenient molecular diversity‐oriented synthesis of various functional sulfur‐containing heterocyclic scaffolds mainly including isothiazole, 2H‐1,3‐thiazine, and thiazolidine via different methods from α‐substituted cyanoacetamides is described. The target molecules have been identified on the basis of analytical spectral data, which may serve as useful structural subunits in the fields of drug discovery.

show abstract

Section: Resultsmentioning

confidence: 99%

Convenient Structural Diversity‐Guided Synthesis of Functionalized Sulfur‐Containing Heterocycles via α‐Substituted Cyanoacetamides

2016

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…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%

“…One example is triphosgene, which is incredibly similar to thiophosgene in terms of its effectiveness toward the synthesis of aryl isothiocyanates. 13 Although triphosgene is fatal if inhaled, it is still considered safer to use than thiophosgene 23 (Scheme 4).…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Synthesis of Isothiocyanates: An Update

Eschliman¹,

Bossmann

2019

Synthesis

View full text Add to dashboard Cite

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

show abstract

“…In the continuation of our ongoing program to develop efficient reagents for the conversion of amines to isothiocyanates, [28] this article describes ferrous sulfate as a novel catalyst for the synthesis of isothiocyanates (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%