Dimethyl Sulfoxide as Methyl Source for the Synthesis of Quinazolinones under Metal‐Free Conditions DOI
Jiwei Wu, Xiaoxiao Yu,

Liangchen Zhong

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(8)

Опубликована: Июль 8, 2022

Abstract An efficient synthesis of biologically important quinazolinones via using dimethyl sulfoxide as a synthon has been developed. This reaction proceeds smoothly to obtain the corresponding products in good yield under metal free conditions and shows an excellent functional group tolerance. A preliminary mechanistic study indicates that C2 hydrogen synthesized heterocycles come from sulfoxide.

Язык: Английский

NaN(SiMe3)2/CsTFA Copromoted Aminobenzylation/Cyclization of 2-Isocyanobenzaldehydes with Toluene Derivatives or Benzyl Compounds: One-Pot Access to Dihydroquinazolines and Quinazolines DOI
Xianghe Meng,

Xue-Cen Xu,

Zhuo Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(5), С. 3156 - 3166

Опубликована: Фев. 14, 2022

A NaN(SiMe3)2/CsTFA copromoted aminobenzylation/cyclization reaction of 2-isocyanobenzaldehydes with toluene derivatives or benzyl compounds has been developed. The works a broad range and compounds, provides simple efficient strategy for the synthesis 4-benzyl-substitued dihydroquinazoline quinazoline from easily available acyclic starting materials in single step. Further applications, including quinazoline, dihydroindolo[1,2-c]quinazoline, dihydro-8H-isoquinolino[2,3-c]quinazoline, demonstrated tremendous potential tandem reaction.

Язык: Английский

Процитировано

14

Iridium-Catalyzed Acceptorless Dehydrogenative Coupling of 2-Aminoarylmethanols with Amides or Nitriles to Synthesize Quinazolines DOI

Hongling Shui,

Yuhong Zhong, Nianhua Luo

и другие.

Synthesis, Год журнала: 2022, Номер 54(12), С. 2876 - 2884

Опубликована: Янв. 31, 2022

Abstract An efficient iridium-catalyzed acceptorless dehydrogenative coupling (ADC) reaction for the preparation of various quinazolines from 2-aminoarylmethanols and amides or nitriles had been developed. A wide range substituted 2-aminobenzyl alcohols (hetero)aryl alkyl benzamides were well compatible to afford in excellent yields. Merits this new strategy are high atom-economy, mild conditions, simple operation, methodology is suitable a variety substrates.

Язык: Английский

Процитировано

13

Synthesis of Substituted Pyrimido[1,2‐b]indazoles through (3+2+1) Cyclization of 3‐Aminoindazoles, Ketones, and N,N‐Dimethylaminoethanol as One‐Carbon Synthon DOI

Zemin Qin,

Renchao Ma,

Shenpeng Ying

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(18), С. 3263 - 3272

Опубликована: Авг. 20, 2022

Abstract 2‐Mono‐ or 2,3‐disubstituted pyrimido[1,2‐ b ]indazoles are synthesized by a (3+2+1) three‐component cyclization of 3‐aminoindazoles, ketones, and N,N ‐dimethylaminoethanol as methine source. The reaction demonstrates good tolerance both aromatic aliphatic well various substitution patterns in air. A plausible mechanism is discussed. magnified image

Язык: Английский

Процитировано

13

Alternative method to Baeyer–Villiger oxidation of cyclobutenones using I2/DMSO catalytic systems DOI
Yi-Chen Sun, Zhibin Hu, Jing Peng

и другие.

Green Chemistry, Год журнала: 2023, Номер 25(18), С. 7079 - 7083

Опубликована: Янв. 1, 2023

A novel and efficient approach utilizing I 2 /DMSO catalytic systems for the Baeyer–Villiger oxidative rearrangement of cyclobutenones was developed.

Язык: Английский

Процитировано

8

Cu(II)-Catalyzed [3 + 1 + 1 + 1] Cyclization of 1,3-Diketones and 2-Naphthols Using N,N-Dimethylethanolamine as a Dual Carbon Synthon for the Synthesis of 2H-Chromenes DOI

Meiqi Geng,

Minzhao Huang,

Jinqiang Kuang

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 89(1), С. 152 - 162

Опубликована: Дек. 12, 2023

Reactions with diverse C1 synthons to realize homologation were well explored. However, homologations occurring twice one synthon in a reaction less reported. We disclose herein Cu(II)-catalyzed novel and efficient synthesis of 2H-chromenes from 2-naphthols, 1,3-diketones, N,N-dimethylethanolamine (DMEA) as dual carbon synthon. Various different functional groups are constructed moderate good yields. This is the first report that DMEA acts

Язык: Английский

Процитировано

7

Rh(III)-Catalyzed Tandem Reaction Access to (Quinazolin-2-yl)methanone Derivatives from 2,1-Benzisoxazoles and α-Azido Ketones DOI
Shan Liu,

An‐Jing Wang,

Min Li

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(16), С. 11253 - 11260

Опубликована: Авг. 8, 2022

A Rh(III)-catalyzed tandem reaction for the synthesis of (quinazolin-2-yl)methanone derivatives has been explored from 2,1-benzisoxazoles and α-azido ketones. The transformation involves denitrogenation ketones, aza-[4 + 2] cycloaddition, ring opening, dehydration aromatization processes. Notably, cycloaddition an imine rhodium complex intermediate with is key to this reaction.

Язык: Английский

Процитировано

9

A Palladium-Catalyzed Carbonylative Acetylation of N-Phenylpyridin-2-amine Using DMF and CO as the Acetyl Source DOI

Jiawei Xu,

Xuan Li, Shoucai Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 6168 - 6175

Опубликована: Апрель 20, 2023

This study reports a carbonylative acetylation for the synthesis of N-phenyl-N-(pyridin-2-yl)acetamides using N,N-dimethylformamide (DMF) as methyl source and CO carbonyl source. Interestingly, dimethyl sulfoxide (DMSO) can be also used when only DMSO solvent. Mechanistic studies DMSO-d6 revealed that group was derived from DMF instead mixed These results indicated preferential

Язык: Английский

Процитировано

4

Iron-Catalyzed [2+1+2+1] Annulation of Amines and N,N-Dimethyl Enaminones using N,N-Dimethylaminoethanol as a One-Carbon Synthon for the Synthesis of 1,4-Dihydropyridines DOI
Jianyong Yuan,

Wanqian Ma,

Qiulin Kuang

и другие.

Synthesis, Год журнала: 2024, Номер 56(12), С. 1932 - 1940

Опубликована: Янв. 9, 2024

Abstract A simple and efficient method for the synthesis of 1,4-dihydropyridines from amines, N,N-dimethyl enaminone N,N-dimethylaminoethanol in a four-component [2+1+2+1] annulation catalyzed by FeCl3 has been established, where was applied as methine source. The procedure executed smoothly, resulting wide range with moderate to good yields. Additionally, these fluorophores exhibited photophysical characteristics.

Язык: Английский

Процитировано

1

Recent Achievements in Organic Reactions in DMSO DOI
Yuan Peng, Jia‐Chen Xiang, An‐Xin Wu

и другие.

Опубликована: Март 8, 2024

In this chapter, we have summarized some special and representative transformations using DMSO as a green solvent in organic synthesis over the last 5 years. contrast to previous reviews, focus more on situ activation pattern of by summarizing different fragmentation processes show reaction initiation pathway. For example, Pummerer-type, Selectfluor-enabled, electrocatalytic-enabled, photocatalytic-enable were classified discussed detail. each pattern, several recent are listed, along with their selected products generality, while detailed mechanism is also provided after example facilitate reader's understanding illustrate chemical principles. We believe that chapter provides unique perspective lead better DMSO-mediated integrated information for researchers who keen select method activation.

Язык: Английский

Процитировано

1

Facile Synthesis of 2-Substituted Quinazolines via Ruthenium(II)-Catalyzed Acceptorless Dehydrogenative Coupling DOI

Shulei Wu,

Qianqian Lei,

Zaoduan Wu

и другие.

Current Organic Chemistry, Год журнала: 2024, Номер 28(4), С. 305 - 318

Опубликована: Фев. 1, 2024

Abstract:: This study aims to develop a practical and facile one-pot synthesis of 2- substituted quinazolines. Using commercially available structurally simple ruthenium( II) complex as the catalyst synthesize series quinazoline derivatives via acceptorless dehydrogenative coupling. The mechanism this reaction was explored by control DFT calculation. protocol offers access diverse array (52 examples) in moderate excellent yields (29%-98%). In summary, we have developed an efficient ruthenium (II)-catalyzed ADC under air atmosphere. only produces hydrogen water by-products, serving sustainable atom-efficient synthetic approach.

Язык: Английский

Процитировано

1