93415-79-3Relevant articles and documents
A photoredox-neutral Smiles rearrangement of 2-aryloxybenzoic acids
Gonzalez-Gomez, Jose C.,Ramirez, Nieves P.,Lana-Villarreal, Teresa,Bonete, Pedro
supporting information, p. 9680 - 9684 (2017/11/30)
We report on the use of visible light photoredox catalysis for the radical Smiles rearrangement of 2-aryloxybenzoic acids to obtain aryl salicylates. The method is free of noble metals and operationally simple and the reaction can be run under mild batch or flow conditions. Being a redox neutral process, no stoichiometric oxidants or reductants are needed.
5-Nitroisocoumarins from tandem Castro-Stephens coupling-6-endo-dig cyclisation of 2-iodo-3-nitrobenzoic acid and arylethynes and ring-closure of methyl 2-alkynyl-3-nitrobenzoates with electrophiles
Woon, Esther C.Y.,Dhami, Archana,Mahon, Mary F.,Threadgill, Michael D.
, p. 4829 - 4837 (2007/10/03)
Reaction of 2-iodo-3-nitrobenzoic acid with arylalkynyl copper(I) reagent gave 3-aryl-5-nitroisocoumarins. Castro-Stephens coupling was followed by in situ Cu-catalysed ring-closure. 1H NMR and X-ray crystallography showed the cyclisations to be 6-endo, contrasting with reports of 5-exo cyclisation of analogous 2-iodobenzoate esters with alkynes. Sonogashira couplings of methyl 2-iodo-3-nitrobenzoate with phenylacetylene and with trimethylsilylacetylene gave the corresponding 2-alkynyl-3-nitrobenzoate esters. With HgSO4, the phenylalkyne underwent 6-endo cyclisation to give 5-nitro-3-phenylisocoumarin. The disubstituted alkyne esters gave 4-phenylselenylisocoumarins with PhSeCl. 5-Nitro-3-phenyl-4-phenylselenylisocoumarin shows significant sterically-driven distortion of the isocoumarin ring. Reaction of methyl 3-nitro-2-phenylethynylbenzoate with ICl gave the 4-iodoisocoumarin. Thus the nitro group tends to direct these electrophile-driven cyclisations towards the 6-endo mode.
A new synthesis of 'push-pull' naphthalenes by condensation of nitro-2-methylbenzoate esters with dimethylacetamide dimethyl acetal
Wong, See-Mun,Shah, Bhavini,Shah, Priyal,Butt, Ian C.,Woon, Esther C.Y.,Wright, James A.,Thompson, Andrew S.,Upton, Christopher,Threadgill, Michael D.
, p. 2299 - 2302 (2007/10/03)
Whereas condensation of 2-methyl-3-nitrobenzoate esters with dimethylformamide dimethyl acetal gives 5-nitroisocoumarin, analogous condensation with dimethylacetamide dimethyl acetal proceeds via a different route, affording 1-methoxy-3-dimethylamino-5-ni