Isothiocyanates in the chemistry of heterocycles

Direct and Facile Synthesis of Acyl Isothiocyanates from Carboxylic Acids Using Trichloroisocyanuric Acid/Triphenylphosphine System

“…Preparation of the reagents in these methods suffers from difficult procedures and the reactions take long time. Conversion of trialkylsilyl carboxylates to acyl isothiocyanates was also reported by using Ph 3 P(SCN) 2 (Ref. 18).…”

“…[4][5][6][7][8][9][10][11][12][13][14] which are mainly based on the reaction of acyl halides with thiocyanate ion. 2,6 Acyl halides are not always easy to access or store. As acyl halides are highly sensitive to moisture and require care in handling, these methods need to anhydrous conditions and long reaction time.…”

“…6 The reaction of carbonimidoyl dichloride with metal thiocyanate is also another reported method of preparation of acyl isothiocyanates, but the starting material is not easily available and the yield of the reaction is too low. 15 There are few reports on the direct conversion of carboxylic acids to acyl isothiocyanates using acid activators such as Ph 3 P(SCN) 2 (Ref. 16) and PO(NCS) 3 (Ref.…”

Design, Synthesis, and Evaluation of ω‐(Isothiocyanato)alkylphosphinates and Phosphine Oxides as Antiproliferative Agents

“…[11] In addition to antiproliferative activity,s ome ITCs exhibit antibacterial activity [12] and can also be used as fungicides or herbicides. [13] ITCs playa ni mportant role in organic synthesis, especially in the synthesis of heterocyclic compounds, [14] including thioamides [15] or thiourea-derived organocatalysts. [16] Among the naturali sothiocyanates such as benzyl isothiocyanate (BITC), phenethyl isothiocyanate (PEITC), or allyl isothiocyanate (AITC), sulforaphane( SFN)-1-(isothiocyanate)-4-(methylsulfinyl)butane (Figure 1) is the most extensively studied ITC.…”

Reactivity and diverse synthetic applications of acyl isothiocyanates

“…Isothiocyanates, well-known as a key reagent in the Edman peptide sequencing, 4 are very useful synthons in organic chemistry, especially in the architecture of heterocycles such functionalized thiazoles, thiadiazoles, triazoles, benzimidazoles, dithiolane, spiro-fused oxazolines, triazines, and oxazines, etc. [5][6][7][8][9][10][11] The methods of synthesis of isothiocyanates have drawn attention of chemists.…”