One-Pot Reaction Sequence: N-Acylation/Pictet-Spengler Reaction/Intramolecular [4 + 2] Cycloaddition/Aromatization in the Synthesis of ß-Carboline Alkaloid Analogues.

One-pot synthesis of tetrahydro-ß-carbolines, fused with an isoindole core, was proposed starting from maleic anhydride and azomethines easily available from tryptamines and 3-(hetaryl)acroleins. This sequence includes four key steps: an acylation of the aldimine with maleic anhydride, a Pictet-Spengler cyclization, an intramolecular Diels-Alder reaction, and a concluding [1,3]-H shift. As a result, six- or seven-nuclear alkaloid-like heterocyclic systems, containing a benzo[1,2]indolizino[8,7-b]indole fragment annulated with furan, thiophene, or pyrrole, are formed in a diastereoselective manner.

Correction: Rhodium(II)-catalyzed transannulation approach to N-fluoroalkylated indoles.

Correction for 'Rhodium(II)-catalyzed transannulation approach to N-fluoroalkylated indoles' by Olga Bakhanovich et al., Org. Biomol. Chem., 2023, https://doi.org/10.1039/d3ob01415k.

Rhodium(II)-catalyzed transannulation approach to N-fluoroalkylated indoles.

Copper(I)-catalyzed cycloaddition of substituted cyclohexenyl acetylenes with azido(per)fluoroalkanes afforded 4-cyclohexenyl-substituted N-(per)fluoroalkylated 1,2,3-triazoles. Their rhodium(II)-catalyzed transannulation led to fused N-(per)fluoroalkyl pyrroles and subsequent oxidation provided N-(per)fluoroalkyl indoles.

Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes.

The rhodium-catalyzed transannulation of N-perfluoroalkyl-1,2,3-triazoles with aromatic and aliphatic terminal alkynes under microwave heating conditions afforded N-perfluoroalkyl-3,4-disubstituted pyrroles (major products) and N-fluoroalkyl-2,4-disubstituted pyrroles (minor products). The observed selectivities in the case of the reactions with aliphatic alkynes were high.

Synthesis, Stability and Reactivity of α-Fluorinated Azidoalkanes.

Organic α-fluorinated azidoalkanes appeared in the literature for the first time half a century ago. However, for a long time they remained undeveloped and were regarded as chemical curiosities. Recent advances in the preparation of α-fluorinated azidoalkanes as well as studies on their stability and reactivity opened up their broader synthetic potential for the preparation of valuable fluorinated and non-fluorinated compounds.