One-pot synthesis of N-substituted 2-methyl-4,5,6,7-tetrahydroindole derivatives

Tanyeli, Cihangir
Yazicioglu, EY
We describe the preliminary results of one-pot syntheses of various N-substituted 2-methyl-4,5,6,7-tetrahydroindole derivatives from 2-(2-bromoailyl)cyclohexanone and the corresponding primary amines in good yields. Aliphatic amines were directly converted to tetrahydroindoles, whereas aromatic amines needed an extra base treatment step to complete the transformation.


A novel one-pot, three-component reaction for the synthesis of isocoumarin-condensed pyrazoles
OZCAN, Sevil; Dengiz, Çağatay; DELIOMEROGLU, Murat K.; ŞAHİN, Ertan; BALCI, METİN (Elsevier BV, 2011-03-30)
The one-pot, three-component reaction of substituted homophthalic anhydrides with hydrazine in DMF as solvent and reactant, at reflux temperature, afforded isochromeno[3,4-c]pyrazole-5(2H)-one derivatives in high yields. The mechanism and roles of the substrates were investigated and it was found that cyclic hydrazides were formed as intermediates.
Synthesis of various camphor-based chiral pyridine derivatives
Tanyeli, Cihangir; Isik, M (Elsevier BV, 2004-07-19)
(+)-beta-Hydroxymethylenecamphor 1 and enamines 2a-e were transformed into chiral camphor-based pyridine derivatives 3a-e via a tandem condensation reaction in good yields.
Intermolecular heterocyclization of alkynones with 2-mercaptoacetaldehyde under metal-free conditions: synthesis of 2,3-disubstituted thiophenes
Vatansever, Erol Can; Kilic, Kubra; Ozer, Merve Sinem; KOZA, GANİ; Menges, Nurettin; Balcı, Metin (Elsevier BV, 2015-09-30)
A concise and regioselective approach for the synthesis of 2,3-disubstituted thiophene derivatives has been developed. The synthetic strategy relies on the reaction of an in situ generated 2-mercaptoacetaldehyde with various alkynones. Furthermore, we calculated the energy gap between the HOMO and the LUMO orbitals of all compounds and observed that the introduction of a strong electron-withdrawing group decreased the HOMO-LUMO energy gap.
High temperature bromination. Part 18: Bromination of benzonorbornadiene derivatives: Polybrominated benzonorbornenes and benzonorbornadienes
Dastan, A; Balcı, Metin (Elsevier BV, 2005-06-06)
The low and high temperature bromination reactions of bromobenzonorbornadiene derivatives were studied and the possible role of a neighboring group in rearrangements was investigated. New polybrominated benzonorbornadiene and benzonorbornene derivatives were synthesized. All compounds were characterized property Using NMR spectroscopy.
An effective new synthesis of 2-aminopyrrole-4-carboxylates
Demir, Ayhan Sıtkı; Emrullahoglu, M (Elsevier BV, 2005-10-31)
Efficient syntheses of 2-aminopyrroles are presented starting from beta-dicarbonyl compounds, bromoacetonitrile, and amines. Alkylation of beta-dicarbonyl compounds with bromoacetonitrile furnished alpha-cyanomethyl-beta-dicarbonyl compounds. The condensation reaction of alpha-cyanomethyl-beta-dicarbonyl compounds with amines catalyzed by p-TsOH affords the corresponding enamines in good yields. Base catalyzed cyclization via the addition of an amine moiety to the carbon-nitrogen triple bond of nitrile furn...
Citation Formats
C. Tanyeli and E. Yazicioglu, “One-pot synthesis of N-substituted 2-methyl-4,5,6,7-tetrahydroindole derivatives,” TETRAHEDRON LETTERS, pp. 9627–9629, 2004, Accessed: 00, 2020. [Online]. Available: