54064-35-6Relevant academic research and scientific papers
Synthesis of Branched Tryptamines via the Domino Cloke-Stevens/Grandberg Rearrangement
Salikov, Rinat F.,Trainov, Konstantin P.,Levina, Anastasia A.,Belousova, Irina K.,Medvedev, Michael G.,Tomilov, Yury V.
, p. 790 - 795 (2017/04/26)
The rearrangement of cyclopropylketone arylhydrazones generated in situ from arylhydrazine hydrochlorides and ketones leads to formation of tryptamine derivatives. The use of (2-arylcyclopropyl)ethanones in the reactions with model 4-bromophenylhydrazine hydrochloride gives branched tryptamines with aryl groups in the α-position to the amino group, while (2-methylcyclopropyl)ethanone gives a mixture of α- and β-substituted products in a ratio of 1:3. The method was found effective in the synthesis of enantiomerically pure tryptamine. Thus, (R,R)-(2-phenylcyclopropyl)ethanone gives the (S)-α-phenyltryptamine derivative with an enantiomeric excess over 99%.
Novel synthesis of substituted cyclopropane acetic acid ethyl esters from cyclopropyl alkyl ketones
Nongkhlaw, Rishan Lang,Nongrum, Ridaphun,Nongkynrih, Irona,Vattakunnel, Felix Mathew,Myrboh, Bekington
, p. 1054 - 1057 (2007/10/03)
The cyclopropane acetic acid ethyl esters 2 have been conveniently prepared in one step from cyclopropyl alkyl ketones 1 by reacting with lead (IV) acetate in triethyl orthoformate in the presence of 70% perchloric acid. In all these reactions triethyl or
A Simple Synthesis of 2-Cyclopentenone: Synthesis of Dihydrojasmone and α-Cuparenone
Anand, R. C.,Ranjan, H.
, p. 673 - 674 (2007/10/02)
A simple synthesis of substituted 2-cyclopentenone has been illustrated through the syntheses of dihydrojasmone and α-cuparenone.The route involves elaboration of α,β-unsaturated ketone to 2-cyclopentenone through (i) methylene transfer to double bond, (ii) nucleophilic ring-opening by thiophenoxide anion, (iii) chlorination of thioether and (iv) generation of carbonyl group from α-chlorothioether to afford 1,4-diketone which subsequently cyclises with alkali to the desired 2-cyclopentenone.
