Synthesis of Triazolo[4′,5′:4,5]furo[2,3-c]pyridine via Post Modification of an Unusual Groebke–Blackburn–Bienaymé Multicomponent Reaction DOI Creative Commons

Aashima Batra,

Manpreet Kaur,

Deepender Kaushik

и другие.

ACS Omega, Год журнала: 2024, Номер 9(27), С. 29372 - 29378

Опубликована: Июнь 24, 2024

The Groebke–Blackburn–Bienaymé (GBB) reaction is a well-established three-component for synthesizing imidazofused scaffolds from heterocyclic amidines, aldehydes, and isonitriles. However, the replacement of pyridoxal as an aldehyde component in this results formation furo[2,3-c]pyridine skeleton "unusual GBB product". Despite interesting nature unusual reaction, not much work was further reported. present research investigates optimization strategy synthesis novel tricyclic triazolo[4′,5′:4,5]furo[2,3-c]pyridines via diazotization 2,3-diamino-furo[2,3-c]pyridines specifically synthesized utilizing chemistry tert-alkyl isocyanide.

Язык: Английский

Cascade Pd-Catalyzed Azide-Isocyanide Cross Coupling/Cyclization/Lactamization Reactions for the Synthesis of Tricyclic Guanidine-Containing Polyheterocycles DOI
Xiaoming Ma, Zhiwei Gao,

Jiawei Niu

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 11, 2025

A one-pot synthesis of a tricyclic guanidine scaffold is developed. The azido-bearing [3 + 2] adducts are used for cascade azide-isocyanide cross-coupling/nucleophilic cyclization/lactamization to afford highly condensed polyheterocycles. wide range azido-containing and isocyanides tolerated in the sequential reactions.

Язык: Английский

Процитировано

1
The Groebke–Blackburn–Bienaymé (GBB) Reaction: A Powerful Tool for Generating Diverse Heterocyclic Scaffold Libraries in Anticancer Drug Discovery DOI
K. L. A. Khan, Rashid Ali,

Shahnaaz Khatoon

и другие.

European Journal of Medicinal Chemistry, Год журнала: 2025, Номер 291, С. 117629 - 117629

Опубликована: Апрель 12, 2025

Язык: Английский

Процитировано

1
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

и другие.

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 1839 - 1879

Опубликована: Авг. 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.

Язык: Английский

Процитировано

5
One-Pot Regioselective Synthesis of Spiroimidazolidinones via a Sequential Ugi 4CR/Azide-Isocyanide Coupling/Cyclization/Rearrangement/Hydroxylation Reaction DOI

Yan‐Mei Yan,

Hongbo Tong, Zhenxing Ren

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 24, 2025

Herein a novel and robust methodology to spiroimidazolidinones has been developed under mild reaction. The reaction of (Z)-2-azido-3-phenylacrylic acids 1, aldehydes 2, amines 3, isocyanides 4, 6 produced regioselectively in 71–88% yields via sequential Ugi 4CR/Pd(0) catalyzed azide-isocyanide coupling/cyclization/rearrangement/hydroxylation Furthermore, the easily accessible starting materials, high bond-forming efficiency, broad substituent tolerance make this strategy useful synthetic medicinal chemistry.

Язык: Английский

Процитировано

0
New efficient synthesis of polysubstituted benzo[d]pyrido[1′,2':1,2]imidazo[4,5-f][1,3]diazepines and pyrido[2′,1':2,3]imidazo[1,5-c]quinazolin-7-ium salts via Groebke-Blackburn-Bienaymé/Staudinger/aza-Wittig/carbodiimide-mediated annulation sequence DOI

Long Zhao,

Mao-Lin Yang,

Hao Chen

и другие.

Tetrahedron, Год журнала: 2024, Номер 152, С. 133834 - 133834

Опубликована: Янв. 9, 2024

Язык: Английский

Процитировано

2
A retro-Mannich mediated transformation of Morita–Baylis–Hillman ketones to saturated imidazo[1,2-a]pyridines DOI

SACHIN SHARMA,

Ajit Kumar Jha,

Srinivasan Easwar

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(11), С. 3137 - 3150

Опубликована: Янв. 1, 2024

Two fruits felled with one stone! – a proof of mechanism and synthetic method that delivers privileged heterocyclic motif.

Язык: Английский

Процитировано

2
One-Step Construction of 1,3,4-Oxadiazoles with Anticancer Activity from Tertiary Amines via a Sequential Copper(I)-Catalyzed Oxidative Ugi/aza-Wittig Reaction DOI Creative Commons
Mei Sun,

Nong-Qi Mao,

Sheng-Long Wang

и другие.

Molecules, Год журнала: 2024, Номер 29(6), С. 1253 - 1253

Опубликована: Март 12, 2024

An unparalleled copper(I)-catalyzed synthesis of 1,3,4-oxadiazoles from tertiary amines in one step has been described. The one-pot reactions involving (N-isocyanimine)triphenylphosphorane, amines, and carboxylic acids resulted the formation moderate to good yields through a consecutive oxidative Ugi/aza-Wittig reaction, enabling direct functionalization sp

Язык: Английский

Процитировано

1
Facile synthesis of dihydroisobenzofuran derivatives via a one-pot sequential Passerini-azide/Ag(I)-catalyzed cyclization process DOI

Yan Luo,

Haifeng Yu,

Yang Li-na

и другие.

Tetrahedron, Год журнала: 2024, Номер 158, С. 133984 - 133984

Опубликована: Апрель 13, 2024

Язык: Английский

Процитировано

0
Phytotoxicity Study of (Amino)imidazo[1,2-a]pyridine Derivatives Toward the Control of Bidens pilosa, Urochloa decumbens, and Panicum maximum Weeds DOI Creative Commons
Luan A. Martinho, Daniel Mário de Lima,

Victor H. J. G. Praciano

и другие.

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 28, 2024

In this work, several imidazo[1,2-a]pyridines were synthesized through the Groebke–Blackburn–Bienaymé three-component reaction (GBB-3CR), and their phytotoxicity was evaluated in vitro by influence on growth of wheat coleoptiles three important agricultural seeds (Allium cepa, Lactuca sativa, Solanum lycopersicum) at test concentrations 1000, 300, 100, 30, 10 μM. A structure–activity relationship established, showing importance halogen groups ortho position attached aromatic ring presence a cyclohexylamine group for greater activity. Post-modification some GBB-3CR adducts carried out, leading to imidazo[1,2-a]pyridine-tetrazole hybrids, which also these bioassays. The seed germination bioassays demonstrated that A. cepa most susceptible seed, affected parameters root shoot lengths. active compound against Bidens pilosa, Urochloa decumbens, Panicum maximum weeds under hydroponic conditions assess its phytotoxic potential more advanced level Promising results achieved, factor inhibition growth, stimulus noted, making it promising hit search new herbicides.

Язык: Английский

Процитировано

0
Synthesis of Triazolo[4′,5′:4,5]furo[2,3-c]pyridine via Post Modification of an Unusual Groebke–Blackburn–Bienaymé Multicomponent Reaction DOI Creative Commons

Aashima Batra,

Manpreet Kaur,

Deepender Kaushik

и другие.

ACS Omega, Год журнала: 2024, Номер 9(27), С. 29372 - 29378

Опубликована: Июнь 24, 2024

The Groebke–Blackburn–Bienaymé (GBB) reaction is a well-established three-component for synthesizing imidazofused scaffolds from heterocyclic amidines, aldehydes, and isonitriles. However, the replacement of pyridoxal as an aldehyde component in this results formation furo[2,3-c]pyridine skeleton "unusual GBB product". Despite interesting nature unusual reaction, not much work was further reported. present research investigates optimization strategy synthesis novel tricyclic triazolo[4′,5′:4,5]furo[2,3-c]pyridines via diazotization 2,3-diamino-furo[2,3-c]pyridines specifically synthesized utilizing chemistry tert-alkyl isocyanide.

Язык: Английский

Процитировано

0