528836-77-3

Upstream product

• 463-71-8 thiophosgene 
• 13141-38-3 2-phenylethynylaniline 
• 75-15-0 carbon disulfide 
• 207278-66-8 2-(phenylethynyl)-(N-triphenylphosphoranylidene)-phenylamine 
• 615-43-0 2-iodophenylamine 
• 536-74-3 phenylacetylene 
• 2926-29-6 Langlois reagent 

Downstream Products

• 143360-82-1 3-(4-chlorophenyl)-2-phenyl-1H-indole 
• 5834-42-4 3-(4-methoxyphenyl)-2-phenyl-1H-indole 
• 3469-20-3 2,3-diphenyl-1H-indole 
• 1357381-20-4 C₁₉H₂₀N₂S 
• 1357381-29-3 C₁₉H₂₀N₂S 
• 1357381-39-5 C₁₉H₂₀N₂S 
• 1446474-30-1 (4E)-2-(N,N-diethylamino)-4-(1-iodobenzylidene)-4H-benzo[d][1,3]thiazine 

Relevant academic research and scientific papers

A silver(i)-catalyzed cascade bicyclization strategy for synthesis of 5: H -benzo [d] tetrazolo[5,1- b] [1,3]thiazines

A simple and efficient protocol for silver(i)-catalyzed tandem reaction of o-alkynylphenyl isothiocyanates with sodium azide has been developed, affording a series of 5H-benzo[d]tetrazolo[5,1-b][1,3]thiazines in moderate to good yields. In this transformation, a [3 + 2] cycloaddition reaction mechanism was involved and two new rings were formed in one pot.

Copper(ii)-catalyzed tandem cyclization for the synthesis of benzo[d][1,3]thiazin-2-yl phosphonates involving C-P and C-S bond formation

A copper(ii)-catalyzed, high-efficiency and atom-economical synthesis of valuable organophosphorus compoundsviatandem cyclization ofo-alkynylphenyl isothiocyanates with phosphites is described. This protocol, having a good functional-group compatibility, provides a simple and direct pathway to organophosphorus heterocycles in good yields under mild conditions. The method could be efficiently scaled up to gram scale, thus providing a potential application of this cascade cyclization strategy in synthesis.

Organophosphine-free copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur

A copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur in the absence of organophosphine has been established. This approach represents a simple and efficient one-pot synthesis of isothiocyanates, and features excellent functional group tolerance and the use of a cheap, safe and odorless sulfur source. Moreover, this process could directly provide isothiocyanate analogous bioactive molecules, thiocarbonyl-containing pesticides and facile construction of benzoxazole and benzimidazole frames.

Isothiocyanate synthesized by three components and preparation method of isothiocyanate

The invention discloses isothiocyanate and a preparation method thereof. The method comprises the steps that primary amine, sodium difluorobromoacetate and elemental sulfur are taken as reactants forreaction; the reaction is carried out under the action of a copper catalyst, wherein the copper catalyst is any one of cuprous chloride, copper bromide, cuprous iodide, copper chloride and copper trifluoromethanesulfonate; an alkali is also added, wherein the alkali is any one of sodium bicarbonate, potassium carbonate, cesium carbonate, potassium phosphate, DABCO and sodium tert-butoxide; the whole reaction is carried out in a solvent, wherein the solvent is acetonitrile or dimethyl sulfoxide, the reaction temperature is 80-120 DEG C, and the reaction time is 10-14 hours. The method can directly synthesize the target product, does not need to separate intermediate products and only needs stirring and heating reaction under normal pressure to obtain the target product, and the yield can beup to 87%; a waste solution is fewer during the reaction, and the method protects the environment and ensures the health of an operator; in addition, a series of isothiocyanate derivatives can be prepared, and the method has a stronger substrate universality.

One-Pot Copper-Catalyzed Cascade Bicyclization Strategy for Synthesis of 2-(1H-Indol-1-yl)-4,5-dihydrothiazoles and 2-(1H-Indol-1-yl)thiazol-5-yl Aryl Ketones with Molecular Oxygen as an Oxygen Source

An atom-economical method for synthesizing N-heterocyclic indoles from readily available o-alkynylphenyl isothiocyanates and propargylamine derivatives is reported. This method involves a copper-catalyzed cascade bicyclization process consisting of an int

Isothiocyanation of amines using the Langlois reagent

The Langlois reagent was found to be effective for the isothiocyanation of primary amines in the presence of copper iodide and diethyl phosphonate.

Nickel Catalysis Enables Hetero [2+2+1] Cycloaddition between Yne-Isothiocyanates and Isonitriles with Low Catalyst Loading

Nickel(II) can be used to catalyze the hetero [2+2+1] cycloaddition of 2-alkynylaryl isothiocyanates and isonitriles in 2-methyltetrahydrofuran (2-MeTHF) to give a wide array of thieno[2,3-b]indoles in excellent yields. The reaction is featured by employi

Triflic acid-promoted cycloisomerization of 2-alkynylphenyl isothiocyanates and isocyanates: A novel synthetic method for a variety of indole derivatives

A new approach towards the synthesis of indole derivatives via triflic acid-promoted cycloisomerization with rearrangement of 2-(alkyn-1-yl)phenyl isothiocyanates and 2-(alkyn-1-yl)phenyl isocyanates has been achieved. By this methodology, structurally di

Cascade radical reactions via α-(arylsulfanyl)imidoyl radicals: Competitive [4 + 2] and [4 + 1] radical annulations of alkynyl isothiocyanates with aryl radicals

Aryl radicals react with 2-(2-phenylethynyl)phenyl isothiocyanate through a novel radical cascade reaction entailing formation of α-(arylsulfanyl)imidoyl radicals and affording a new class of compounds, i.e. thiochromeno[2,3-b]indoles. These derivatives are formed as mixtures of substituted analogues arising from competitive [4 + 2] and [4 + 1] radical annulations. The isomer ratio is strongly dependent on the aryl substituent and is correlated to its capability to delocalize spin density. The presence of a methylsulfanyl group in the ortho-position of the initial aryl radical results in complete regioselectivity and better yields, as the consequence of both strong spindelocalization effect, which promotes exclusive [4 + 1] annulation, and good radical leaving-group ability, which facilitates aromatization of the final cyclohexadienyl radical. Theoretical calculations support the hypothesis of competitive, independent [4 + 2] and [4 + 1] annulation pathways. They also suggest that rearrangement onto the sulfur atom of the [4 + 1] intermediate does not occur via a sulfuranyl radical but rather through either a transition state or a sulfur-centered (thioamidyl) radical; the latter is possibly the preferred route in the presence of an o-methylsulfanyl moiety that can act as a leaving group in the final ipso-cyclization process.