210880-58-3

Upstream product

• 615-43-0 2-iodophenylamine 
• 1066-54-2 trimethylsilylacetylene 
• 54467-95-7 1-azido-2-iodo-benzene 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 

Downstream Products

• 669090-69-1 1-azido-2-ethynyl-benzene 
• 1403495-29-3 2,3-bis(4-bromophenyl)-1H-indole 

Relevant academic research and scientific papers

Facile and efficient synthesis of [1,4]oxazino[3,2-b]indoles and 1H-pyrazino[2,3-b]indoles through gold-catalyzed cascade cyclization of (azido)ynamides

[1,4]Oxazino[3,2-b]indoles as well as 1H-pyrazino[2,3-b]indoles are constructed in good to excellent yields via gold-catalyzed cascade cyclization of (azido)ynamides. The use of readily available starting materials, a simple procedure and mild reaction co

Photopromoted Entry to Benzothiophenes, Benzoselenophenes, 3H-Indoles, Isocoumarins, Benzosultams, and (Thio)flavones by Gold-Catalyzed Arylative Heterocyclization of Alkynes

Visible light-promoted and gold-photoredox-catalyzed reactions of heteroatom (N, S, Se, O) tethered alkynes with arenediazonium salts selectively proceeded to build vicinal diaryl-substituted 2H-benzo[e][1,2]thiazine 1,1-dioxides (benzosultams), benzoselenophenes, benzothiophenes, 4H-chromen-4-ones (flavones), 3H-indoles, 1H-isochromen-1-ones (isocoumarins), and 4H-thiochromen-4-ones (thioflavones). Moreover, the utility of functionalized 3H-indoles as precursors for further elaboration has been demonstrated with the switchable and facile preparation of 1H-indoles, 2-oxindoles, and 3-oxindolines. (Figure presented.).

A novel heterocumulenic Pauson-Khand reaction of alkynylcarbodiimides: A facile and efficient synthesis of heterocyclic ring-fused pyrrolinones

The first examples of the heterocumulenic Pauson-Khand reaction are described. Alkynylcarbodiimides undergo an intramolecular Pauson-Khand cycloaddition upon heating in the presence of Mo(CO)6 and DMSO to afford 4,5-dihydro-1H-pyrrolo[2,3-b]pyrrolin-2-ones and 1H-pyrrolo[2,3-b]indol-2-ones.

Photolysis of regioisomeric diazides of 1,2-diphenylacetylenes studies by matrix-isolation spectroscopy and DFT calculations.

A series of diazides of 1,2-diphenylacetylenes was photolyzed in matrices at low temperature and transient photoproducts were characterized by using IR, UV/vis methods combined with ESR studies. Theoretical calculations were also used to understand the experimental findings. The introduction of phenylethynyl groups on phenyl azides has little effect on the photochemical pathway. Thus, upon photoexcitation, (phenylethynyl)phenyl azides afforded the corresponding triplet nitrene, which is in photoequilibrium with the corresponding azacycloheptatetraene. In marked contrast, azidophenylethynyl groups exhibited a dramatic effect not only on the photochemical pathway of phenyl azides but also on the electronic and molecular structure of the photoproducts. The patterns of the effect depended upon the relative position of azide groups in the diphenylacetylene unit. Whenever two azide groups were situated in a conjugating position with respect to each other, as in p,p'-, o,o'-, and p,o'-bis(azides), the azides always resulted in the formation of a quinoidal diimine diradical in which unpaired electrons were extensively delocalizedin the pi-conjugation. The situation changed rather dramatically when azide groups were introduced in the meta position. Thus, the formation of azacycloheptatetraene was noted in the photolysis of the m.m'-isomer. ESR studies indicated the generation of a quintet state that was shown to be a thermally populated state with a very small energy gap of ca. 100 cal mol(-1). The m,p'-isomer was shown to be an excellent precursor for the high-spin quintet dinitrene.The IR spectra of the photoproduct showed no bands ascribable to azacycloheptatetraene. The observed spectra were in good agreement with that calculated for the quintet state. Strong EPR signals assignable to the quintet state were observed, along with rather weak signals due to mononitrenes. Moreover, the quintet bis(nitrene) was rather photostable under these conditions.

A study of vinyl radical cyclization onto the azido group by addition of sulfanyl, stannyl, and silyl radicals to alkynyl azides

Thermal radical reactions of azidoalkynes 2, 8, 14, and 21a-c with thiols 1a-c afford 2-sulfanylvinyl radicals by selective addition of sulfanyl radicals to the triple bond. 1-Phenylvinyl radicals 23 and 30a, as well as vinyl radical 30b, undergo fast 5-cyclization onto the aromatic azide function to give cyclized indoles. In contrast, both 1-phenyl (15, 17) and 1-alkyl (3a,b, 9) vinyl radicals fail to add to their aliphatic azido substituents and exclusively undergo cyclization onto the aromatic sulfanyl ring and H transfer from the thiol precursor. Azidoalkynes 14 and 21a react with Bu3SnH and TMSS under radical conditions to give instead the corresponding amines as a result of preferential attack of Bu3Sn · and (TMS)3Si · radicals on the azido group rather than on the triple bond. Evidence is provided that alkyl radical cyclizations onto azides are not feasible in the presence of thiol, in contrast with the reported utility of these cyclization reactions in the presence of Bu3SnH and TMSS.