Efficient Synthesis of Highly Fused Quinazolinone Derivatives via Multiple C−C Bond Formations and 1,4‐Palladium Migration DOI
Sampath Thavaselvan, Natarajan Arumugam, Abdulrahman I. Almansour

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(6)

Published: Dec. 9, 2023

Abstract An efficient palladium‐catalyzed annulation of 3‐arylquinazolinones with mono and double alkyne insertion was developed for the synthesis fused quinazolinone derivatives in 43–80 % yields. A notable effect observed product yield, when bases/additives were modulated. The reaction mechanism is believed to proceed through C−X cleavage/alkyne insertion/1,4‐Pd migration C−H a one‐pot manner.

Language: Английский

Regioselective [3+2]‐Spiroannulation and [4+n]‐Annulation Approaches through Activation of C−H Bond Facilitated by Ru(II) as Catalyst: Role of Solvent Selectivity DOI
Rahul Dev Mandal, Anindita Sarkar, Dwaipayan Das

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1863 - 1876

Published: Feb. 21, 2024

Abstract Ru(II)‐catalyzed and solvent‐switched [3+2]‐spiroannulation [4+n] (n=1, 2, 3) annulations of 2‐aryl quinazolinone or 2‐aryl‐2,3‐dihydrophthalazine‐1,4‐diones with ynones alkynyl alcohol 1,3‐diynes under mild reaction conditions have been analyzed. These reactions take place in the presence appropriate solvent features a redox‐neutral pathway. Ynone serves as an ‘atypical one‐carbon unit’ [4+1] annulation generates tetrasubstituted carbon center bearing diverse heterocycles through [3+2] strategies. Post transformations synthesized spiro‐products augments potential developed methodology.

Language: Английский

Citations

4
Alkoxycarbonylation-triggered nitrile insertion/remote C(sp2)–H and C(sp3)–H functionalization to access esterified quinazolinones and amidines DOI

Shao-Qun Cai,

Hui-Xin Xiao,

Shi-Cui Fang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3861 - 3867

Published: Jan. 1, 2024

A new alkoxycarbonyl radical triggered nitrile insertion/remote C(sp 2 )–H and 3 functionalization reaction is developed.

Language: Английский

Citations

2
Ru(II)‐Catalyzed ortho C—H Allylation of N‐Aryl‐7‐azaindoles with 2‐Methylidene Cyclic Carbonate DOI
Jing Zhang,

Quanjian Luo,

Han‐Chi Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(9), P. 985 - 989

Published: Dec. 26, 2023

Comprehensive Summary A Ru(II)‐catalyzed ortho allylation reaction of N ‐aryl‐7‐azaindole with readily available 2‐methylidene cyclic carbonate has been developed. This is an effective pathway for synthesizing 7‐azaindole derivatives a wide scope substrates and high yields. In addition, the method can be extended to other heterocyclic compounds several carbonates, highlighting practicality this strategy synthesis.

Language: Английский

Citations

4
Acyclic nucleosides via allylic amination of 2-methylidenetrimethylene carbonate with N-heteroaromatics DOI
Kexin Huang, Zhaoyang Chen,

Feng-Yi Lai

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 158, P. 133991 - 133991

Published: April 15, 2024

Language: Английский

Citations

1
A sustainable approach to microwave assisted synthesis of 2-(het)/arylquinazolin-4(3H)-ones via ionic liquid supported Cu(II) catalyst DOI
Md Gulzar Ahmad, Balamurali MM, Kaushik Chanda

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 146, P. 155182 - 155182

Published: Aug. 1, 2024

Language: Английский

Citations

1
Tandem annulation and dipolar cycloaddition of azomethine imines in catalytic C(sp2)–H functionalization DOI
Neeraj Kumar Mishra, Amitava Rakshit,

Kyeongwon Moon

et al.

Bulletin of the Korean Chemical Society, Journal Year: 2023, Volume and Issue: 45(2), P. 131 - 144

Published: Dec. 12, 2023

Abstract The synthesis and functionalization of privileged nitrogen heterocycles has emerged as a central topic in drug discovery material science. In this context, the tandem C–H intramolecular annulation received prodigious attention, it is able to expedite construction heteroaromatic frameworks beyond conventional functionalization. general, significant effort been made develop [3 + 2] dipolar cycloaddition azomethine imines with π‐unsaturated compounds. Moreover, 3], [4 2 2], [5 3] reactions various dipolarophiles have demonstrated. To date, however, combination catalytic cyclization using both directing groups units less explored. This review focuses on recent progress toward azomethines range coupling partners.

Language: Английский

Citations

3
Efficient Synthesis of Highly Fused Quinazolinone Derivatives via Multiple C−C Bond Formations and 1,4‐Palladium Migration DOI
Sampath Thavaselvan, Natarajan Arumugam, Abdulrahman I. Almansour

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(6)

Published: Dec. 9, 2023

Abstract An efficient palladium‐catalyzed annulation of 3‐arylquinazolinones with mono and double alkyne insertion was developed for the synthesis fused quinazolinone derivatives in 43–80 % yields. A notable effect observed product yield, when bases/additives were modulated. The reaction mechanism is believed to proceed through C−X cleavage/alkyne insertion/1,4‐Pd migration C−H a one‐pot manner.

Language: Английский

Citations

1