A new strategy for 2-substituted indolylalkylamines: synthesis of 2-aryldihomotryptamines

Synthesis of tryptamines by the Fischer method using synthetic precursors and latent forms of amino-butanal (review)

“…Methods for the Fischer synthesis of 2-substituted tryptamines and homotryptamines (see, for example, the recent papers [8][9][10]) will hardly be discussed at all this review since on the whole they have fewer limitations [2]. Methods for their synthesis have also been examined in the reviews [2,5,[11][12][13][14].…”

One-step synthesis of 2-indolylalkylamines

“…This approach can be effected in one step without using protecting groups. [9][10][11] In contrast to 3 indolylalkylamines, which can be syn thesized in well developed ways, 2 indolylalkylamines (isotryptamines) are studied much more poorly for lack of accessible synthetic methods. Acylamides of 2 indolyl alkylamines (isomelatonins) have been obtained in many steps by acylation of prepared isotryptamines.…”

“…Com pounds 2a,b were prepared as described earlier. 10 7 Amino 1 phenylheptan 2 one hydrochloride (2a …”

Synthesis of substituted tryptamines and their homologs: A new aspect in the Fischer reaction

“…Scheme 2 R = H, Hal, Alk, OAlk Application of this approach (earlier, no aliphatic amino ketones were employed in the Fischer reaction) allowed substituted dihomotryptamines to be obtained in Scheme 1 one step from accessible 6 aminohexanones in high yields. 19 To determine the area of application of this method for the synthesis of substituted tryptamines, we studied in the present work the effect of the nature of the amino carbonyl compound (the character of the substituent and the length of the aminoalkyl fragment) on the pathway of the Fischer reaction. For this purpose, we prepared a number of cyclic imines and amino ketones.…”

“…For this purpose, we prepared a number of cyclic imines and amino ketones. The synthe ses of the starting reagents, namely, 6 aminohexanones, 19 five membered cyclic imines, 20 and 3 acyllactams, 21 were described by us earlier; six and seven membered imines were prepared according to the published procedure. 22 The Fischer indole synthesis involves the formation of arylhydrazones of carbonyl compounds followed by their rearrangements.…”