50463-86-0Relevant academic research and scientific papers
InBr3/Cu(OTf)2-catalyzed C-alkylation of pyrroles and indoles with α-diazocarbonyl compounds
Yadav,Reddy,Satheesh
, p. 8331 - 8334 (2003)
Pyrroles and indoles react smoothly with α-diazocarbonyl compounds in the presence of 10 mol% of InBr3 under mild conditions to afford the corresponding 2- and 3-alkyl pyrrole and 3-alkyl indole derivatives, respectively, in good yields with high selectivity.
Asymmetric transfer hydrogenation of heterocycle-containing acetophenone derivatives using N-functionalised [(benzene)Ru(II)(TsDPEN)] complexes
Barrios-Rivera, Jonathan,Xu, Yingjian,Clarkson, Guy J.,Wills, Martin
supporting information, (2021/12/02)
The application of enantiomerically-pure ruthenium(II) catalysts containing N - functionalised TsDPEN ligand to the asymmetric transfer hydrogenation of 15 examples of α-heterocyclic acetophenone derivatives is reported. Products of up to 99% ee were formed.
Synthesis of 2-alkylidenepyrrolidines, pyrroles, and indoles by condensation of silyl enol ethers and 1,3-bis-silyl enol ethers with 1-azido-2,2-dimethoxyethane and subsequent reductive cyclization
Bellur, Esen,Goerls, Helmar,Langer, Peter
, p. 4751 - 4761 (2007/10/03)
The condensation of 1,3-bis-silyl enol ethers with 1-azido-2,2- dimethoxyethane and subsequent reductive cyclization allowed an efficient regio- and diastereoselective synthesis of a variety of 2-alkylidene-4- methoxypyrrolidines. The thermal elimination of methanol resulted in the formation of functionalized pyrroles. Similarly, 2,3,3a,4,5,6-hexahydro-2,3- benzopyrroles were prepared and transformed into 4,5,6,7-tetrahydro-2,3- benzopyrroles. In contrast, treatment of 2-alkylidenepyrrolidines with trifluoroacetic acid resulted in formation of indoles by [4 + 2] cycloaddition and subsequent extrusion of a nitrogen atom.
Phenanthroindolizidine and Related Alkaloids: Synthesis of Tylophorine, Septicine, and Deoxytylophorinine
Cragg, John E.,Herbert, Richard B.,Jackson, Frederick B.,Moody, Christopher J.,Nicolson, Ian T.
, p. 2477 - 2486 (2007/10/02)
Tylophorine (1) is synthesized in two ways.The first method begins with the synthesis of the amide-ester (7), which on reaction, successively, with triethyloxonium fluoroborate and sodium borohydride, gives the aminoester (8) selectively; hydrolysis and polyphosphoric acid-catalysed ring-closure of compound (9) gives the ketone (10) which yields tylophorine (1) on Clemmensen reduction.An alternative approach is by a biogenetically patterned sequence which involves condensation of (3,4-dimethoxybenzoyl)acetic acid (26) with 1-pyrroline (24) generated either in situ from putrescine by pea-seedling diamine oxidase or from ornithine by oxidation with N-bromosuccinimide; the product (16) condenses with 3,4-dimethoxyphenylacetaldehyde in benzene to give an enamine .This undergoes cyclisation and dehydration in methanol; sodium borohydride reduction then gives the alkaloid septicine (19) which, on oxidation with thallium(III) trifluoroacetate, yields tylophorine (1).Deoxytylophorinine (34) is made in an exactly analogous manner to the latter method for tylophorine.
