Molecular editing of pyrroles via a skeletal recasting strategy

X Zhou, Q Huang, J Guo, L Dai, Y Lu - ACS Central Science, 2023 - ACS Publications
Heterocyclic scaffolds are commonly found in numerous biologically active molecules,
therapeutic agents, and agrochemicals. To probe chemical space around heterocycles …

Recent advancements in pyrrole synthesis

SC Philkhana, FO Badmus, IC Dos Reis, R Kartika - Synthesis, 2021 - thieme-connect.com
This review article features selected examples on the synthesis of functionalized pyrroles
that were reported between 2014 and 2019. Pyrrole is an important nitrogen-containing …

Controllable skeletal and peripheral editing of pyrroles with vinylcarbenes

Y Yang, Q Song, P Sivaguru, Z Liu… - Angewandte Chemie …, 2024 - Wiley Online Library
The skeletal editing of azaarenes through insertion, deletion, or swapping of single atoms
has recently gained considerable momentum in chemical synthesis. Here, we describe a …

Ring contraction methodology for the synthesis of pyrroles

U Joshi, M Pipelier, S Naud… - Current Organic …, 2005 - ingentaconnect.com
Ring contraction of larger rings is one of the important tools in the repertoire of the methods
for the synthesis of pyrroles and has long been described in the literature. This methodology …

Dearomative ring expansion of polycyclic arenes

P Piacentini, TW Bingham, D Sarlah - Angewandte Chemie, 2022 - Wiley Online Library
Benzocycloheptenes constitute a common structural motif embedded in many natural
products and biologically active compounds. Herein, we report their concise preparation …

Skeletal editing: interconversion of arenes and heteroarenes

BW Joynson, LT Ball - Helvetica Chimica Acta, 2023 - Wiley Online Library
Skeletal editing involves making specific point‐changes to the core of a molecule through
the selective insertion, deletion or exchange of atoms. It thus represents a potentially …

Unified access to pyrimidines and quinazolines enabled by N–N cleaving carbon atom insertion

EE Hyland, PQ Kelly, AM McKillop… - Journal of the …, 2022 - ACS Publications
Given the ubiquity of heterocycles in biologically active molecules, transformations with the
capacity to modify such molecular skeletons with modularity remain highly desirable. Ring …

Skeletal editing of pyrimidines to pyrazoles by formal carbon deletion

GL Bartholomew, F Carpaneto… - Journal of the American …, 2022 - ACS Publications
A method for the conversion of pyrimidines into pyrazoles by a formal carbon deletion has
been achieved guided by computational analysis. The pyrimidine heterocycle is the most …

Synthesis of dienes from pyrrolidines using skeletal modification

H Qin, T Guo, K Lin, G Li, H Lu - Nature Communications, 2023 - nature.com
Saturated N-heterocyclic pyrrolidines are common in natural products, medicinal
compounds and agrochemicals. However, reconstruction of their skeletal structures creating …

Selective skeletal editing of polycyclic arenes using organophotoredox dearomative functionalization

P Ji, CC Davies, F Gao, J Chen, X Meng… - Nature …, 2022 - nature.com
Reactions that lead to destruction of aromatic ring systems often require harsh conditions
and, thus, take place with poor selectivities. Selective partial dearomatization of fused …