Main Chain 1,5-Disubstituted-1H-Tetrazole-Based Polymers via Ugi-Azide-Four-Multicomponent Polymerization (UA-4MCP) DOI

Meryem S. Akdemir,

Birgit Huber, Marina Simian

et al.

ACS Applied Polymer Materials, Journal Year: 2023, Volume and Issue: 5(8), P. 6643 - 6650

Published: Aug. 1, 2023

The utilization of the distinctive molecular architecture tetrazoles, which comprises a five-membered ring containing four nitrogen atoms, offers tremendous potential in field polymer chemistry. Although research on pendant chain tetrazole-containing polymers has been considerably reported, exploration advanced synthesis methods for main tetrazole-based not extensively undertaken. On this premise, 1,5-disubstituted-1H-tetrazole (1,5-DS-T)-based compounds was investigated to showcase possibility formation by using Ugi-azide-four-multicomponent polymerization (UA-4MCP) strategy. Particularly, UA-4MC were designed with various side groups (e.g., aliphatic or aromatic) and engineered post-polymerization modification via thiol-ene photo-click reaction. chemical characterization confirmed 1,5-DS-T-based number average mass (Mn) up 8500 g mol–1. Importantly, side-group variation permitted tuning glass-transition temperature (Tg) between −25 60 °C. Furthermore, exhibited moderate thermal stability 305 ± 10 °C besides interesting nonconventional fluorescence behavior.

Language: Английский

Sequential enantioselective Ugi-4CR/post-Ugi transformation strategy: a precise construction of structurally diverse azaspiro polycyclic scaffolds DOI
Xiaobao Wu,

Jun‐Xiu Shi,

Yi‐Ming Ou

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 67(2), P. 576 - 586

Published: Oct. 23, 2023

Language: Английский

Citations

4
Enantioselective Access to Chiral 2,5-Diketopiperazines via Stereogenic-at-Cobalt(III)-Catalyzed Ugi-4CRs/Cyclization Sequences DOI
Fang Wei, Bingbing Sun,

Shi-Cheng Qin

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(22), P. 16024 - 16037

Published: Nov. 2, 2023

An asymmetric synthesis of chiral 2,5-diketopiperazines by the Ugi-4CR/cyclization is exhibited. The employment catalytic anionic Co(III) complexes delivered α-propiolyl aminoamides in high yields with excellent enantioselectivities (31 examples, up to 95% ee). following treatment Ugi-adducts PPh3 leads 2,5-DKPs without significant loss (26 91%

Language: Английский

Citations

4
Crystal Clear: Decoding Isocyanide Intermolecular Interactions through Crystallography DOI Creative Commons

Eleftheria Chatziorfanou,

Atilio Reyes Romero, Lotfi Chouchane

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(2), P. 957 - 974

Published: Jan. 4, 2024

The isocyanide group is the chameleon among functional groups in organic chemistry. Unlike other multiatom groups, where electrophilic and nucleophilic moieties are typically separated, isocyanides combine both functionalities terminal carbon. This unique feature can be rationalized using frontier orbital concept has significant implications for its intermolecular interactions reactivity of group. In this study, we perform a Cambridge Crystallographic Database-supported analysis intramolecular to investigate solid state, excluding isocyanide–metal complexes. We discuss examples different interaction classes, including as hydrogen bond acceptor (RNC···HX), halogen bonding (RNC···X), involving carbon atoms (RNC···C). latter serves an intriguing illustration Bürgi–Dunitz trajectory represents crucial experimental detail well-known multicomponent reactions such Ugi- Passerini-type mechanisms. Understanding spectrum that undergo holds fields medicinal chemistry, materials science, asymmetric catalysis.

Language: Английский

Citations

1
Recent Synthetic Developments of Asymmetric Multicomponent Transformations: Strecker, Mannich, Passerini and Ugi Reactions DOI Creative Commons
Marcelo H. R. Carvalho, Giovanni W. Amarante, Pedro P. de Castro

et al.

Journal of the Brazilian Chemical Society, Journal Year: 2023, Volume and Issue: unknown

Published: Jan. 1, 2023

Multicomponent reactions (MCRs) are important transformations, which allow the attainment of structurally complex derivatives in a single step, starting from three or more compounds with relatively simple structures. These generally associated principles green chemistry, allowing incorporation most (or all) atoms materials products (atom economy) and reducing purification steps (and, consequently, need for solvents waste production). For long time, asymmetric methodologies (in special enantioselective protocols) multicomponent transformations remained gap literature, limiting use these to produce only as racemates low diastereoselectivities. Over last two decades, better comprehension mechanisms allowed development efficient enantio- diastereoselective procedures, attracting interest both academia industry. In this review, selected examples four (Strecker, Mannich, Passerini Ugi) will be discussed, presenting general overview field pointing out possible advantages limitations above mentioned methodologies. some cases, discussions around mechanisms, proposed transition states activation modes detailed disclosed.

Language: Английский

Citations

3
Assembly of iodinated indolo[1,2-c]quinazoline amines via I2/CHP-promoted cascade annulation of isocyanides and diarylalkynes DOI
Min Zhang, Meng Li, Huanfeng Jiang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(17), P. 4305 - 4310

Published: Jan. 1, 2023

A convenient and concise approach to iodinated indolo[1,2- c ]quinazoline amines via I 2 /cumene hydroperoxide (CHP)-promoted cascade annulation of diarylalkynes isocyanides has been established.

Language: Английский

Citations

3
Ammonium carboxylates in the ammonia-Ugi reaction: one-pot synthesis of α,α-disubstituted amino acid derivatives including unnatural dipeptides DOI Creative Commons
Keisuke Tomohara,

Satoru Kusaba,

M. MASUI

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(34), P. 6999 - 7005

Published: Jan. 1, 2024

Using ammonium carboxylates in trifluoroethanol, the ammonia-Ugi reaction proceeded with high yields at room temperature and gave a variety of α,α-disubstituted amino acid derivatives, including unnatural dipeptides.

Language: Английский

Citations

0
Loading Lewis Acid/Base Pair on Metal Nanocluster for Catalytic Ugi Reaction DOI

Jiqiang Fan,

Yanshuang Li,

Wen Wu Xu

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 137(1)

Published: Sept. 13, 2024

Abstract Constructing structurally robust and catalytically active metal nanoclusters for catalyzing multi‐component reactions is an interesting while challenging task. Inspired by Lewis acid base catalysis, we realized the combination of both sites on surface a stable gold nanocluster Au 35 Cd 2 . The catalytic potential in four‐component Ugi reaction was explored, demonstrating high activity exceptional recyclability. In‐depth mechanism studies indicate that synergy acid/base pair crucial efficiency ‐catalyzed reaction. Bearing structure, multiple activation hierarchical chirality, expected to display further performance such as asymmetric catalysis.

Language: Английский

Citations

0
Asymmetric Bromination/Semipinacol Rearrangement Enabled by Brønsted Acids of Stereogenic-at-Cobalt(III) Complexes DOI

Yue Shen,

Hua‐Jie Jiang,

Jie Yu

et al.

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

Published: Oct. 3, 2024

On the basis of chiral ion pair between catalytic anionic stereogenic-at-cobalt(III) complexes and halonium intermediates, an asymmetric halogenation/semipinacol rearrangement reaction has been established using

Language: Английский

Citations

0
Atroposelective synthesis of axially chiral imidazo[1,2- a ]pyridines via asymmetric multicomponent reaction DOI Creative Commons

Shibin Hong,

Wei Liu, Chengmin Zhang

et al.

Science Advances, Journal Year: 2024, Volume and Issue: 10(49)

Published: Dec. 4, 2024

Imidazo[1,2- a ]pyridines are privileged heterocycles with diverse applications in medicinal chemistry; however, the catalytic asymmetric synthesis of these heterocyclic structures remains underexplored. Herein, we present an efficient and modular approach for atroposelective axially chiral imidazo[1,2- via multicomponent reaction. By utilizing phosphoric acid catalyst, Groebke-Blackburn-Bienaymé reaction involving various 6-aryl-2-aminopyridines, aldehydes, isocyanides gave access to wide range ]pyridine atropoisomers high excellent yields enantioselectivities. Extensive control experiments underscored pivotal role remote hydrogen bonding donor on substrates achieving stereoselectivity reactions. The versatile derivatizations atropisomeric products, especially their as analog NOBINs facile conversion into unique 6,6-spirocyclic further emphasize merits this methodology.

Language: Английский

Citations

0
Hyperbranched 5-sulfosalicylic acid-TDI-chitosan decorated by Fe3O4 nanoparticles: a highly efficient solid acid organocatalyst for the synthesis of quinazoline derivatives under green conditions DOI Creative Commons

Reyhaneh Peyvasteh,

Mohammad G. Dekamin, Ehsan Valiey

et al.

Research Square (Research Square), Journal Year: 2023, Volume and Issue: unknown

Published: May 30, 2023

Abstract In this research, a new magnetic decorated hyperbranched chitosan by grafting of 5-sulfosalicylic acid using toluene-2,4-diisocyanate linker (CS-TDI-SSA-Fe3O4) was designed and prepared conveniently. The obtained biopolymeric nanomaterial properly characterized FT-IR, EDX XRD, FESEM, TGA VSM spectroscopic, microscopic, or analytical methods. supramolecular CS-TDI-SSA-Fe3O4 nanocomposite investigated, as heterogeneous solid acidic organocatalyst, to promote three-component synthesis 2,3-dihydroquinazoline-4(1H)-one derivatives under green chemistry conditions. nanocatalyst demonstraed act highly efficient for the various quinazoline derivatives, an important pharmaceutical scaffold, through multicomponent strategy. reaction proceeds very well in presence EtOH afford corresponding high excellent yields. Key advantages present protocol are use renewable biodegredable simple procedure preparation hybrid material. Furthermore, catalyst can be used at least five times with slight decrease its catalytic activity.

Language: Английский

Citations

0