Synthesis of 3-(2-quinolyl) chromones from ynones and quinolineN-oxidesviatandem reactions under transition metal- and additive-free conditions DOI
Jing Liu,

Dan Ba,

Yanhui Chen

et al.

Chemical Communications, Journal Year: 2020, Volume and Issue: 56(29), P. 4078 - 4081

Published: Jan. 1, 2020

A novel method for the synthesis of 3-(2-quinolyl) chromones through a tandem [3+2] cycloaddition/ring-opening/O-arylation from ynones and quinoline N-oxides has been developed. This protocol proceeds under transition metal- additive-free conditions can be amplified to gram level in 91% yield. 3-(1-Isoquinolyl) 3-(2-pyridyl) are also successfully synthesized using isoquinoline pyridine basic conditions. Various heteroarene-contaning were afforded 30-98% yields, which difficult obtained compounds interest pharmaceutical chemistry chemical biology.

Language: Английский

Recent advances in multi-component reactions and their mechanistic insights: a triennium review DOI

Stephy Elza John,

Shivani Gulati, Nagula Shankaraiah

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(15), P. 4237 - 4287

Published: Jan. 1, 2021

This review summarizes the recent developments in MCRs, incorporating different strategies along with their mechanistic aspects.

Language: Английский

Citations

262

A Strategy for Accessing Trifluoromethyl Carbinol-Containing Chromones from o-Hydroxyaryl Enaminones and Trifluoroacetaldehyde/Ketone Derivatives DOI
Siyu Pan, Mengshi Song,

Lingling Zuo

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5586 - 5596

Published: April 6, 2023

Herein, we present a practical strategy for the direct construction of structurally diverse trifluoromethyl carbinol-containing compounds, especially CF3-substituted tertiary alcohol with chromone derivatives from easily available o-hydroxyaryl enaminones and trifluoroacetaldehyde/ketone under metal-free conditions. This reaction features broad substrate scope good yields is scaled up. Notably, one-pot in two-steps obtained products amidines also developed to provide series multi-substituted pyrimidine bearing two unique hydroxyls one containing functional units.

Language: Английский

Citations

53

Dimethyl Sulfoxide: Yesterday's Solvent, Today's Reagent DOI
Zahra Tashrifi,

Mohammad Mohammadi Khanaposhtani,

Bagher Larijani

et al.

Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 362(1), P. 65 - 86

Published: Sept. 20, 2019

Abstract Dimethyl sulfoxide (DMSO) has had a long history of use as polar solvent and active pharmaceutical ingredient in the past decades. However, this decade DMSO attracted attention scientists source oxygen, carbon or sulfur wide range organic reactions. In review, we have summarized classified latest findings area based on applications single dual synthon. magnified image

Language: Английский

Citations

140

C3‐Functionalized Chromones Synthesis by Tandem C−H Elaboration and Chromone Annulation of Enaminones DOI
Leiqing Fu, Jie‐Ping Wan

Asian Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 8(6), P. 767 - 776

Published: April 23, 2019

Abstract Chromone is a heterocyclic entity presents in number of natural products, clinical pharmaceuticals, as well molecules with enriched biological functions. As cutting‐edge area, the synthesis chromones has seen spectacular progress over past decade. Among available synthetic modes toward chromone scaffolds, annulation ortho ‐hydroxyphenyl functionalized N,N ‐disubstituted enaminones turned out to be one most reliable and practical ones. By combining this featured transformation vinyl α‐C−H bond enaminone structure, large tandem reactions providing structurally diverse C3‐functionalization have been recently realized. strategy valuable an important branch enaminone‐based organic synthesis, such are highly instructive for chemistry many other disciplines related moiety. Herein, we present first time research advances on C3‐functionalized via C−H elaboration tertiary enaminones.

Language: Английский

Citations

79

Transition metal-free synthesis of 3-trifluoromethyl chromones via tandem C–H trifluoromethylation and chromone annulation of enaminones DOI
Qing Yu, Yunyun Liu, Jie‐Ping Wan

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(18), P. 2770 - 2775

Published: Jan. 1, 2020

The synthesis of 3-trifluoromethyl chromones has been realized via transition metal-free reactions o-hydroxyphenyl enaminones and the Langlois reagent cascade C–H trifluoromethylation chromone annulation.

Language: Английский

Citations

76

Rongalite as C1 Synthon in the Synthesis of Divergent Pyridines and Quinolines DOI
Huan Gao,

Liyun Zhou,

Jie‐Ping Wan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7188 - 7198

Published: May 12, 2023

Rongalite has been used as a cheap and efficient carbon synthon for the synthesis of divergent N-heteroaromatics, including different pyridines quinolines. The selective products can be achieved by employing enaminones or enaminones/anilines reaction partners. In addition, compared with using conventional aldehyde synthons, rongalite displays an evident advantage in providing considerably higher product yields under milder conditions. GC-MS analysis process performed to probe possible mechanism.

Language: Английский

Citations

32

Recent advances in the diversification of chromones and flavones by direct C H bond activation or functionalization DOI

Shanghui Tian,

Tian Luo,

Yanping Zhu

et al.

Chinese Chemical Letters, Journal Year: 2020, Volume and Issue: 31(12), P. 3073 - 3082

Published: July 26, 2020

Language: Английский

Citations

56

Toward C2-nitrogenated chromones by copper-catalyzed β-C(sp2)–H N-heteroarylation of enaminones DOI

Tian Luo,

Jie‐Ping Wan, Yunyun Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(9), P. 1107 - 1112

Published: Jan. 1, 2020

The synthesis of C2-nitrogenated chromones has been performed via reactions enaminones and nitrogen nucleophiles based on an unconventional β-C–H bond functionalization a featured chromone annulation enaminones.

Language: Английский

Citations

53

Recent Advances in Iodine‐Promoted C−S/N−S Bonds Formation DOI
Honghua Zhang,

Huihong Wang,

Yi Jiang

et al.

Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 26(72), P. 17289 - 17317

Published: May 29, 2020

Abstract Sulfur‐containing scaffold, as a ubiquitous structural motif, has been frequently used in natural products, bioactive chemicals and pharmaceuticals, particularly C−S/N−S bonds are indispensable many biological important compounds pharmaceuticals. Development of mild general methods for formation great significance modern research. Iodine its derivatives have recognized inexpensive, environmentally benign easy‐handled catalysts or reagents to promote the construction under reaction conditions, with good regioselectivities broad substrate scope. Especially based on this, several new strategies, such oxidation relay strategy, greatly developed accelerated advancement this field. This review focuses recent advances iodine promoted hybridized formation. The features mechanisms corresponding reactions summarized results some cases compared those previous reports. In addition, future domain is discussed.

Language: Английский

Citations

51

Rongalite as C1 Synthon and Sulfone Source: A Practical Sulfonylmethylation Based on the Separate-Embedding Strategy DOI
Xiang‐Long Chen, Chun‐Yan Wu,

Jin‐Tian Ma

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 24(1), P. 223 - 227

Published: Dec. 16, 2021

Rongalite has been used in several challenging synthetic transformations with operationally simple and effective protocols. However, the employment of multiple characteristics rongalite chemistry is comparatively little known. Herein we report a separate-embedding type sulfonylmethylation sulfoxonium ylides which concurrently acted as sulfone source, C1 synthon, radical initiator, potential reducing reagent for first time. Notably, this facile easy-handling reaction does not require catalyst or prefunctionalized reagents.

Language: Английский

Citations

45