Employing sulfonyl azide as a nitrogen donor, a visible-light-enabled aerobic dealkylative imidation of tertiary and secondary amines involving C(sp3)–C(sp3) bond cleavage with moderate to excellent yields at room temperature is described. It has been demonstrated that this imidation could take place spontaneously upon visible-light irradiation, and could be facilitated considerably by a ruthenium photocatalyst and oxygen. An alternative mechanism to the previous aerobic photoredox pathway has also been proposed.
Ortho-Quinones represent a special class of redox active compounds associated with a spectrum of pronounced biological activities, including selective cytotoxicity and antimicrobial actions. The modification of the quinone ring by simple nitrogen and sulphur substitutions leads to several new classes of compounds with their own, distinct redox behaviour and equally distinct activities against cancer cell lines and Trypanosoma cruzi. Some of the compounds investigated show activity against T. cru...
#1Babak Kaboudin(IASBS: Institute for Advanced Studies in Basic Sciences)H-Index: 28
#1Babak Kaboudin(IASBS: Institute for Advanced Studies in Basic Sciences)H-Index: 13
Last. Hiroshi Aoyama(Tokyo University of Pharmacy and Life Sciences)H-Index: 9
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In this report, a green synthesis of N-sulfonyl amidines via the direct reaction of tertiary or secondary amines with sulfonyl azides is described. Transition metal- and catalyst-free conditions were used for the synthesis of biologically important N-sulfonyl amidines. Further studies showed that the reaction proceeded via in situ aerobic oxidation of amines under reflux conditions.
#1Binbin Huang(HIT: Harbin Institute of Technology)H-Index: 11
#2Chao Yang(HIT: Harbin Institute of Technology)H-Index: 20
Last. Wujiong Xia(HIT: Harbin Institute of Technology)H-Index: 21
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Reported herein is a straightforward protocol for approaching N-sulphonylamidines via an electricity-driven, iodine-mediated Cross Dehydrogenative Condensation (CDC) between sulphonamides and tertiary amines, which features exclusive N-CH3 selectivity for the amine partners. Mechanistic studies indicate that an in situ generated N-iodoaminium species serves as the key intermediate.
Herein we describe an efficient copper-catalyzed coupling of sulfonamides with alkylamines to synthesize (E)-N-sulfonylformamidines. The reaction is accomplished under mild conditions without use of corrosive acid or base as additive. It tolerates a broad scope of substrates and generates the products with exclusive (E)-stereoselectivity.