Telescoped Flow Synthesis of Azacyclic Scaffolds Exploiting the Chromoselective Photolysis of Vinyl Azides and Azirines

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(38)

Published: May 8, 2024

An efficient chromoselective photochemical process is presented for the synthesis of 2H-azirines and 1,3-diazabicylo[3.1.0]hex-3-enes from readily available vinyl azides. The method exploits continuous flow photochemistry to enable safe consumption hazardous azide group provides uniform irradiation using high-power LEDs at 365-450 nm. Additionally, a scaled telescoped has been developed providing access drug-like 1,6-dihydropyrimidines pyrimidines via integrated ring-expansion oxidation reactions. Given prevalence various azacyclic targets in pharmaceutical, agrochemical materials applications it anticipated that this methodology will further exploitations these important scaffolds.

Language: Английский

Continuous flow synthesis of the antiviral drug tecovirimat and related sp³-rich scaffolds

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Fast, high-yielding syntheses of a medicinally relevant sp 3 -rich polycyclic scaffold have been developed and its synthetic utility demonstrated in range condensation reactions.

Language: Английский

Continuous flow synthesis of alkynes from isoxazolones

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 20, 2024

We present an efficient flow method for the preparation of disubstituted alkynes from isoxazolones under diazotisation conditions. This overcomes reproducibility issues batch variant and safely affords alkyne products on gram scale.

Language: Английский