Instant Macrocyclizations via Multicomponent Reactions

Michael Fragkiadakis

doi:10.1021/acs.joc.3c01379

Instant Macrocyclizations via Multicomponent Reactions

2023-08-19

11

PRE

AI

M

Michael Fragkiadakis

P

Paraskevi-Kleio Anastasiou

M

Marios Zingiridis

M

Marios E. Triantafyllou‐Rundell

A

Atilio Reyes Romero

C

Constantinos C. Stoumpos

C

Constantinos G. Neochoritis *

DOI：10.1021/acs.joc.3c01379

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Abstract

En 中文

Macrocycles fascinate chemists due to both their structure and their applications. However, we still lack efficient and sustainable synthetic methods, giving us straightforward access to them. Herein, a rapid macrocyclization utilizing a two-step, one-pot approach based on orthogonal multicomponent reaction (MCR) tactics is introduced. This synthetic protocol, which is based on Ugi and Groebke-Blackburn-Bienayme ' reactions with isocyanides tethered to alkyl tosylates, yields medium sized macrocycles that are otherwise difficult to achieve. Single crystal structures reveal conformational reorganization via intramolecular hydrogen bonding, and modeling studies profile the synthesized libraries.

Keywords:

UGI-SMILES

MACROCYCLES

ISOCYANIDES

STRATEGIES

CHEMISTRY

DISCOVERY

Instant Macrocyclizations via Multicomponent Reactions

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