Pyridine synthesis by reactions of allyl amines and alkynes proceeding through a Cu(OAc)2 oxidation and Rh(III)-catalyzed N-annulation sequence.
نویسندگان
چکیده
A new methodology has been developed for the synthesis of pyridines from allyl amines and alkynes, which involves sequential Cu(II)-promoted dehydrogenation of the allylamine and Rh(III)-catalyzed N-annulation of the resulting α,β-unsaturated imine and alkyne.
منابع مشابه
A method for the synthesis of pyridines from aldehydes, alkynes and NH4OAc involving Rh-catalyzed hydroacylation and N-annulation.
A new method for regiocontrolled pyridine synthesis has been developed involving sequential Rh(I)-catalyzed chelation-assisted hydroacylation of alkynes with aldehydes followed by Rh(III)-promoted N-annulation of the resulting α,β-enones with another alkyne and NH(3).
متن کاملRhodium-catalyzed direct coupling of biaryl pyridine derivatives with internal alkynes.
Axially chiral biaryls were synthesized by an isoquinoline or 2-pyridine-directed Rh(III)-catalyzed dual C-H cleavage and coupling with internal alkynes in good to excellent yields. Oxidation of isoquinoline derivatives with m-CPBA furnished their corresponding N-oxides, which could be utilized as Lewis base catalysts in asymmetric reactions.
متن کاملRhodium(iii)-catalyzed annulation of arenes with alkynes assisted by an internal oxidizing N-O bond.
Rh(iii)-catalyzed C-H activation of 3-aryl-dihydroisoxazoles in the coupling with diarylacetylenes has been developed under redox-neutral conditions. This reaction occurred under mild conditions with no by-product, and the N-O bond functions as an oxidizing directing group, leading to efficient synthesis of isoquinolines functionalized with a proximal secondary alcohol.
متن کاملSynthesis of 3-alkyl spiro[4,5]trienones by copper-catalyzed oxidative ipso-annulation of activated alkynes with unactivated alkanes.
A Cu-catalyzed oxidative ipso-annulation of activated alkynes with unactivated alkanes for the synthesis of 3-alkyl spiro[4,5]trienones is described. This method allows the formation of two carbon-carbon bonds and one carbon-oxygen bond in a single reaction through a sequence of C-H oxidative coupling, ipso-carbocyclization and dearomatization.
متن کاملCopper-catalyzed annulation of heteroaromatic β-halo-α,β-unsaturated carboxylic acids with alkynes for the synthesis of indolo[2,3-c]pyrane-1-ones and thieno[2,3-c]pyrane-7-ones.
The annulation of heteroaromatic β-halo-α,β-unsaturated carboxylic acids with alkynes proceeds efficiently in the presence of Cu(OAc)2·H2O as a catalyst to afford the corresponding indolo[2,3-c]pyrane-1-ones and thieno[2,3-c]pyrane-7-ones in moderate to good yields. This strategy offers a simple and efficient route for the synthesis of indolo[2,3-c]pyrane-1-ones and thieno[2,3-c]pyrane-7-ones w...
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عنوان ژورنال:
- Chemical communications
دوره 48 92 شماره
صفحات -
تاریخ انتشار 2012