Eight-membered and larger rings DOI
Charles N. Moorefield, George R. Newkome

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 497 - 517

Published: Jan. 1, 2024

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023) DOI Creative Commons
Cristina Martini, Muhammad Idham Darussalam Mardjan, Andrea Basso

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 1839 - 1879

Published: Aug. 1, 2024

The Groebke–Blackburn–Bienaymé (GBB) three-component reaction, discovered in 1998, is a very efficient strategy to assemble imidazo[1,2- ]-heterocycles starting from amidines, aldehydes and isocyanides. This review aims exhaustively describe innovative aspects of this reaction achieved during the last five years, classifies them into categories: synthetic methods, building blocks, scaffolds, biological activities physical properties.

Language: Английский

Citations

5

The Ugi Multicomponent Reaction for the One‐Step Construction of Macrocycles DOI Open Access
Yi‐Ming Chen, Xue Li, Zhigang Xu

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: March 21, 2025

The exploration of macrocycles began in the 20th century, coinciding with progressive advancement synthetic chemistry methodologies. From numerous strategies, Ugi reaction stands out as an efficacious four-component (4-CR). is particularly distinguished by its robust functional group tolerance, enabling creation that are both diverse and complex a singular step. This review collates contemporary examples macrocycles, all which have been crafted using to construct these macrocyclic frameworks. employment various bifunctional reagents (with same or different groups), has introduced plethora cyclization tactics, resulting synthesis multitude cage molecules. In order offer invaluable insights into construction use distinct colors for reactants made entire process transparently visible, thereby enhancing readers' understanding sparking their interest.

Language: Английский

Citations

0

C1 functionalization of imidazo heterocycles via carbon dioxide fixation DOI Creative Commons

Michael Fragkiadakis,

Paraskevi-Kleio Anastasiou,

Ioannis Volyrakis

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(97), P. 14411 - 14414

Published: Jan. 1, 2023

Utilizing CO2 as a one-carbon building block in the preparation of high-value chemical entities is cornerstone modern organic synthesis. Herein, we exemplify this strategy through mild, one-pot methodology that gives rapid access to N-heteroaryl substituted 6-, 8- and 9-membered carbamates via fixation.

Language: Английский

Citations

7

Generation of multimillion chemical space based on the parallel Groebke–Blackburn–Bienaymé reaction DOI Creative Commons

Evgen V Govor,

Vasyl Naumchyk,

Ihor Nestorak

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 1604 - 1613

Published: July 16, 2024

Parallel Groebke-Blackburn-Bienaymé reaction was evaluated as a source of multimillion chemically accessible chemical space. Two most popular classical protocols involving the use Sc(OTf)

Language: Английский

Citations

1

Functional chromophores synthesized via multicomponent Reactions: A review on their use as cell-imaging probes DOI
Brenno A. D. Neto, Jenny E. P. Sorto,

Alexandre A.M. Lapis

et al.

Methods, Journal Year: 2023, Volume and Issue: 220, P. 142 - 157

Published: Nov. 6, 2023

Language: Английский

Citations

3

Multicomponent Reaction-Based Heteroannulations: A Direct Access to Fused Tetrazolo Piperazinones and 1,4-Diazepanones DOI
Constantinos G. Neochoritis, Eirini Fotopoulou,

Alexandros Vasilakis

et al.

Synlett, Journal Year: 2024, Volume and Issue: 35(15), P. 1828 - 1832

Published: Jan. 5, 2024

Abstract By exploiting the chemistry of bifunctional isocyanides, straightforward, rapid, and scalable Ugi-tetrazole-based multicomponent reaction heteroannulations were developed. Our synthetic approach provides a series diverse fused tetrazolo piperazinones 1,4-diazepanones in just one step.

Language: Английский

Citations

0

Origin of Octafluorocyclopentene Polyelectrophilicity DOI
Haowen Tian,

William Lee,

Yuli Li

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(8), P. 5375 - 5382

Published: Feb. 14, 2024

Octafluorocyclopentene (OFCP) has found utility as a polyelectrophile in substitution cascades that form complex macrocyclic compounds. The Harran group synthesis of polypeptides depends on OFCP linker, combining with four different nucleophilic units polypeptide. We report computational investigation the origins reactivity and rationale for controlled mono-, di-, tri-, tetrasubstitution fluoride ions by heteroatomic nucleophiles. roles inductive, negative hyperconjugative, resonance electron-donation substituents are explored reaction OFCP, less-fluorinated analogues, common electrophilic alkenes several

Language: Английский

Citations

0

Unraveling the Potential of Cyclic N‐Sulfonyl Ketimines in the MCR Universe DOI Creative Commons

Michael Fragkiadakis,

Eirini Fotopoulou, Konstantinos G. Froudas

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: July 31, 2024

Abstract Cyclic N ‐sulfonyl ketimines constitute an accessible class of lead‐like heterocycles with a vast application in both synthetic organic and medicinal chemistry. In this context, we harness the capabilities these four different isocyanide‐based multicomponent reactions. Our goal was to create libraries compounds functional groups vectors that are compatible for structural elaboration optimization their physical properties. We synthesized 15 unprecedented high diversity complexity, whereas have obtained single crystal structures each scaffold, unraveling geometrical features potential employment drug discovery.

Language: Английский

Citations

0

Eight-membered and larger rings DOI
Charles N. Moorefield, George R. Newkome

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 497 - 517

Published: Jan. 1, 2024

Citations

0