1598463-34-3

Upstream product

• 941-55-9 4-toluenesulfonyl azide 
• 40307-11-7 1-ethyl-4-ethynylbenzene 

Downstream Products

• 1598463-46-7 N-(2-(4-(diethylamino)phenyl)-2-(4-ethylphenyl)vinyl)-4-methylbenzenesulfonamide 
• 1598463-47-8 N-(2-(4-(diethylamino)phenyl)-2-(4-ethylphenyl)vinyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Acid-catalyzed three-component addition of carbonyl compounds with 1,2,3-triazoles and indoles

A facile and efficient acid-catalyzed three-component reaction of indoles, 1-tosyl-1,2,3-triazoles and carbonyl compounds has been developed. The use of TsOH with a small amount of water significantly promoted the reaction yield. This method provided a general and one-pot approach for the synthesis of structurally diverseC3-alkylated indole derivatives. The alkylation exclusively occurred at theN2position of triazoles. Various functional groups were tolerated under the optimized simple reaction conditions.

Rh-Catalyzed Formal [3+2] Cyclization for the Synthesis of 5-Aryl-2-(quinolin-2-yl)oxazoles and Its Applications in Metal Ions Probes

A facile and efficient strategy for the synthesis of 5-aryl-2-(quinolin-2-yl)oxazoles via rhodium-catalyzed formal [3+2] cyclization of 4-aryl-1-tosyl-1H-1,2,3-triazoles with quinoline-2-carbaldehydes has been described. The protocol employs mild conditions and offers good yields of diverse 2,5-aryloxazole derivatives with a broad reaction scope. It is amenable to gram-scale synthesis and easily transformation. Moreover, this 5-aryl-2-(quinolin-2-yl)oxazole skeleton is indeed a new fluorophore and its applications in metal ions probes are also investigated and showed fluorescent responses to mercury ion.

Synthesis of benzothiazonine by rhodium-catalyzed denitrogenative transannulation of 1-sulfonyl-1,2,3-triazole and thiochromone

A facile synthesis of multi-functionalized benzothiazonine was achieved by the rhodium-catalyzed denitrogenative annulation of 1-sulfonyl-1,2,3-triazole and thiochromone. In view of the excellent atom economy, broad substrate scope and easy availability of starting materials, the protocol provided an efficient strategy for the construction of mediumN,S-heterocycles.

Synthesis of Multifunctionalized 2-Carbonylpyrrole by Rhodium-Catalyzed Transannulation of 1-Sulfonyl-1,2,3-triazole with β-Diketone

A facile rhodium-catalyzed transannulation of 1-sulfonyl-1,2,3-triazoles with β-diketones was realized, and a series of multisubstituted 2-carbonylpyrroles were synthesized efficiently (up to 94% yield). The protocol features several advantages, such as readily available materials, mild reaction conditions, a concise operating procedure, a broad reaction scope, and excellent regioselectivity when benzoylacetone derivatives were used.

Synthesis of β-amino-α,β-unsaturated ketone derivatives via sequential rhodium-catalyzed sulfur ylide formation/rearrangement

In the presence of a Rh(II) catalyst and β-(methylthio)-α,β-unsaturated ketones, 1-sulfonyl-1,2,3-triazoles can be converted into functionalized β-amino-α,β-unsaturated ketones via formation of α-imino rhodium carbene/sulfur ylide and subsequent rearrangement. The products decompose to useful 2-methylthiopyrrole derivatives conveniently in high yield.

Rhodium-Catalyzed Synthesis of 2,5-Epoxybenzo[f][1,4]oxazepines by Tandem Reaction of 1-Sulfonyl-1,2,3-triazoles and Salicylaldehydes

Readily available 1-sulfonyl-1,2,3-triazoles were converted into α-imino carbenes in the presence of catalytic amounts of rhodium(II) salts. The carbenes underwent a tandem reaction with salicylaldehydes to provide a series of functionalized 2,5-epoxybenzo[f][1,4]oxazepines in high yields. A novel protocol for the synthesis of 2,5-epoxybenzo[f][1,4]oxazepines is developed. The complicated ring system can be constructed from readily available N-sulfonyl-1,2,3-triazoles and salicylaldehyde derivatives in a one-pot procedure. Many valuable functional groups are well tolerated in this transformation. [Rh2(piv)4] = dirhodium(II) tetrapivalate.

One-Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides

A general and efficient one-pot aminoethylation of substituted indoles/pyrroles was accomplished for the synthesis of various tryptamine derivatives employing a combination of alkynes and sulfonyl azides as readily accessible aminoethylating agents. The reaction features a successful integration of copper-catalyzed alkyne and azide cycloaddition to N-sulfonyl-1,2,3-triazole, rhodium-catalyzed selective insertion of α-iminocarbenes onto the C3-H bond of indoles, and reduction of the resultant enamides to tryptamine derivatives employing either NaCNBH3 or palladium catalyst, in one-pot. The reaction also showed excellent functional-group tolerance and allowed the synthesis of various substituted tryptamines in good to excellent yield. This transformation constitutes a one-pot formal regioselective functionalization of terminal alkynes. Utility of the synthesized tryptamine was further demonstrated in the synthesis of dihydro-β-carboline and tryptoline.