Brønsted Acid Triggers [6/7 + 1] Cascade Cyclization by N-Alkyl Amine C(sp3)–N Cleavage: Mild Synthesis of Benzo[1,4]oxazepane and Dihydrobenzo[1,5]oxazocine DOI
Lu Yin, Zhou Zhang,

Shuntao Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13629 - 13640

Published: Sept. 2, 2024

A catalyst-free mild synthesis was reported to produce medium-ring oxazepane and oxazocine derivatives from aminomaleimides

Language: Английский

Cu(ii)-catalyzed domino construction of spironaphthalenones by dearomatization of β-naphthols and using N,N-dimethylaminoethanol as a C1 synthon DOI

Meiqi Geng,

Jinqiang Kuang, Maozhong Miao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(15), P. 3101 - 3104

Published: Jan. 1, 2023

Herein, a Cu(II)-catalyzed facile construction of synthetically valuable spiro compounds from β-naphthols in air is reported, which N,N-dimethylaminoethanol (DMEA) serves as an efficient and unique C1 synthon. This transformation proceeds through ortho-quinone methide (o-QM) formation/Michael addition/dearomatization sequence, affording various spiro(naphthalenenaphtho)furan-2-ones moderate to excellent yields.

Language: Английский

Citations

24

Copper-catalyzed divergent construction of naphthofurans and benzochromanes from 2-naphthols, 4-methylene-quinazolin(thi)ones, and N,N-dimethylethanolamine DOI

Meiqi Geng,

Jinqiang Kuang, Weiwei Fang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(4), P. 1198 - 1204

Published: Jan. 1, 2024

Cu( ii )-catalyzed divergent synthesis of naphthofurans and benzochromanes through [3 + 2 1] 1 annulations is established.

Language: Английский

Citations

15

I2-DMSO-Mediated Construction of 2,3- and 2,4-Disubstituted Pyrimido[1,2-b]indazole Skeletons DOI
Linlin Ma, You Zhou,

Yong‐Xing Tang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 3941 - 3953

Published: Feb. 29, 2024

An efficient synthetic method for constructing 2,3- and 2,4-disubstituted pyrimidio[1,2-b]indazole skeletons through I2-DMSO-mediated substrate-controlled regioselective [4 + 2] cyclization is reported. The reaction conditions are mild, its operation simple, the substrate scope wide. More than 60 derivatives have been synthesized, providing a new methodology related molecules potentially enriching bioactive-molecule libraries.

Language: Английский

Citations

6

Transition-Metal Catalyzed Synthesis of Pyrimidines: Recent Advances, Mechanism, Scope and Future Perspectives DOI
Vipin K. Maikhuri, Divya Mathur, Ankita Chaudhary

et al.

Topics in Current Chemistry, Journal Year: 2024, Volume and Issue: 382(1)

Published: Jan. 31, 2024

Language: Английский

Citations

5

Construction of Pyrazolo[1,5-a]pyrimidines and Pyrimido[1,2-b]indazoles with Calcium Carbide as an Alkyne Source DOI

Xinjie You,

Botao Wang, Fei Wen

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(28), P. 5822 - 5826

Published: Jan. 1, 2024

One-step construction of both 5-arylpyrazolo[1,5- a ]pyrimidines and 2-arylpyrimido[1,2- b ]indazoles using inexpensive, abundant easy-to-handle calcium carbide as solid alkyne source is depicted.

Language: Английский

Citations

5

Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders DOI
Jiao Chen, Zihan Zhang, Guojin Sun

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 110050 - 110050

Published: May 28, 2024

Language: Английский

Citations

4

Substrate‐induced Selective α‐C(sp3)−H Activation of N‐alkyl Amines: Synthesis of Coumarin‐fused Quinolinones under Air DOI
Zhou Zhang, Juan Wan, Lu Yin

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1430 - 1435

Published: Jan. 23, 2024

Abstract A substrate‐induced synthesis of coumarin‐fused quinolinones is achieved from 4‐(phenylamino)‐2 H ‐chromen‐2‐ones using N ‐alkyl amines as the solvent and a carbon source under air conditions without any catalysts in one pot. This protocol highlights special roles which were not only used reactants but also an internal oxidant selectively activated ‐ α ‐C( sp 3 )−H bond. reaction features catalyst‐free, broad substrate scopes ( 27 examples 24 examples), operationally simple for one‐step synthesis, recovery recycling solvent.

Language: Английский

Citations

3

I2–DMSO-mediated formal [3 + 1 + 2] synthesis of pyrimido[1,2-b]indazole using 1,4-dithiane-2,5-diol as a surrogate of ethylene DOI

Yong-Dong Du,

Jungang Wang, Jinyi Liu

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: 156, P. 155453 - 155453

Published: Jan. 9, 2025

Language: Английский

Citations

0

Three-component one-pot construction of 2-aryl-3-benzylbenzo[4,5]imidazo[1,2- a ]pyrimidines using solid calcium carbide as an alkyne source DOI

Jiao Wang,

Zhiqiang Wang, Botao Wang

et al.

Synthetic Communications, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 11

Published: Feb. 16, 2025

Language: Английский

Citations

0

Sustainable Synthesis of Polyfluoro-Pyrimido [1,2-a] Benzimidazole Derivatives Using a Tandem Strategy─Ultrasound and an Integrated Continuous Flow System DOI Creative Commons

Vijay Thavasianandam Seenivasan,

Nian‐Qi Chen, Karthick Govindan

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 6, 2025

We have developed a novel ultrasound technique that generates significant amounts of CF3-substituted benzo[4,5] imidazo [1,2-a]pyrimidine analogues from easily accessible starting materials in an ecologically friendly and efficient approach. This method is notably helpful for producing physiologically relevant compounds containing the imidazopyrimidine unit, which serves as versatile building block synthesis N-fused heterocycles devoid metals, solvents, additives, catalysts. Additionally, utilizing open-air environment, range polyfluoro-ynones were successfully reacted with 2-aminobenzimidazole, generating diverse array polyfluoroimidazo[1,2-a]pyrimidine derivatives. Furthermore, by employing integrated flow system approach, we able to synthesize polyfluoro-substituted benzo[4,5]imidazo[1,2-a]pyrimidine derivatives alkynes much shorter reaction time. Gram-scale proved this method's scalability highlighted its potential synthetic industrial applications. The straightforward nature process, broad compatibility various functional groups, substantial sustainability advantages collectively underscore significance.

Language: Английский

Citations

0