Recent advances in catalytic synthesis of medium-ring lactones and their derivatives

2021 ◽  
Author(s):  
Zi-Kui Liu ◽  
Yang Gao ◽  
Xiao-Qiang Hu
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Catalytic Synthesis ◽  
Efficient Synthesis ◽  
Recent Advances ◽  
Medium Ring

Medium-sized lactones are widely found in various natural products and pharmaceuticals. However, the efficient synthesis of these sturtures remains as a challenging topic in organic synthesis due to the disfavored...

scholarly journals Recent Advances in the Catalytic Synthesis of Imidazolidin-2-ones and Benzimidazolidin-2-ones

Catalysts ◽  
2019 ◽  
Vol 9 (1) ◽  
pp. 28 ◽  
Author(s):  
Alessandra Casnati ◽  
Elena Motti ◽  
Raffaella Mancuso ◽  
Bartolo Gabriele ◽  
Nicola Della Ca’
Keyword(s):  
Natural Products ◽  
Carbonyl Group ◽  
Ring Expansion ◽  
Catalytic Synthesis ◽  
Chiral Auxiliaries ◽  
Aziridine Ring ◽  
Urea Derivatives ◽  
Structural Motifs ◽  
Recent Advances ◽  
Direct Incorporation

2-Imidazolidinone and its analogues are omnipresent structural motifs of pharmaceuticals, natural products, chiral auxiliaries, and intermediates in organic syntheses. Over the years, continuous efforts have been addressed to the development of sustainable and more efficient protocols for the synthesis of these heterocycles. This review gives a summary of the catalytic strategies to access imidazolidin-2-ones and benzimidazolidin-2-ones that have appeared in the literature from 2010 to 2018. Particularly important contributions beyond the timespan will be mentioned. The review is organized in four main chapters that identify the most common approaches to imidazolidin-2-one derivatives: (1) the direct incorporation of the carbonyl group into 1,2-diamines, (2) the diamination of olefins, (3) the intramolecular hydroamination of linear urea derivatives and (4) aziridine ring expansion. Methods not included in this classification will be addressed in the miscellaneous section.

scholarly journals Recent Advances in Organocatalyzed Asymmetric Synthesis of Benzopyran and Benzodihydropyran (Chromane) Nuclei

Symmetry ◽  
2019 ◽  
Vol 11 (12) ◽  
pp. 1510
Author(s):  
Renato Dalpozzo ◽  
Raffaella Mancuso
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Organic Synthesis ◽  
Building Blocks ◽  
Core Structure ◽  
The Core ◽  
Recent Advances ◽  
Set Up

Benzopyran and benzodihydropyran (chromane) nuclei are the core structure of many natural products, in particular flavonoids. Many compounds possessing this structure are nutraceuticals, pharmaceutical nutrients. Therefore, benzopyran and chromane scaffolds are important building blocks in organic synthesis and many efforts have been made to set up efficient methods for their synthesis. In particular, asymmetric methods are of great importance, being natural products, and generally chiral substances. This review aims to cover literature in the range 2017–first half of 2019.

scholarly journals The allylic chalcogen effect in olefin metathesis

2010 ◽  
Vol 6 ◽  
pp. 1219-1228 ◽  
Author(s):  
Yuya A Lin ◽  
Benjamin G Davis
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Chemical Biology ◽  
Positive Influence ◽  
Efficient Synthesis ◽  
Cross Metathesis ◽  
Allyl Sulfide ◽  
Hydroxy Groups ◽  
Allyl Sulfides

Olefin metathesis has emerged as a powerful tool in organic synthesis. The activating effect of an allylic hydroxy group in metathesis has been known for more than 10 years, and many organic chemists have taken advantage of this positive influence for efficient synthesis of natural products. Recently, the discovery of the rate enhancement by allyl sulfides in aqueous cross-metathesis has allowed the first examples of such a reaction on proteins. This led to a new benchmark in substrate complexity for cross-metathesis and expanded the potential of olefin metathesis for other applications in chemical biology. The enhanced reactivity of allyl sulfide, along with earlier reports of a similar effect by allylic hydroxy groups, suggests that allyl chalcogens generally play an important role in modulating the rate of olefin metathesis. In this review, we discuss the effect of allylic chalcogens in olefin metathesis and highlight its most recent applications in synthetic chemistry and protein modifications.

Recent advances in the application of tetrabromomethane in organic synthesis

2021 ◽  
Author(s):  
Tharmalingam Punniyamurthy ◽  
Sandeep Kumar ◽  
Tariq A Shah
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Value Added ◽  
Recent Advances

Tetrabromomethane (CBr4) is a multitasking agent and can be utilized as a catalyst, mediator and reagent in the synthesis of value added chemicals, natural products, pharmaceuticals and materials. CBr4, as...

Recent advances in the catalytic synthesis of 3-aminooxindoles: an update

2020 ◽  
Vol 18 (25) ◽  
pp. 4692-4708 ◽  
Author(s):  
Jasneet Kaur ◽  
Banni Preet Kaur ◽  
Swapandeep Singh Chimni
Keyword(s):  
Natural Products ◽  
Catalytic Synthesis ◽  
Biologically Active Compounds ◽  
Core Structure ◽  
Biologically Active ◽  
Active Compounds ◽  
The Core ◽  
Recent Advances

3-Substituted-3-aminooxindoles are versatile scaffolds and these motifs constitute the core structure of number of natural products and biologically active compounds.

Recent Advance on Benzofuranones: Synthesis and Transformation via C-H Functionalization

Synthesis ◽  
2021 ◽  
Author(s):  
Zhi Tang ◽  
Zhou Tong ◽  
Shuang-Feng Yin ◽  
Nobuaki Kambe ◽  
Renhua Qiu
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Organic Synthesis ◽  
Building Blocks ◽  
Efficient Synthesis ◽  
Bond Functionalization ◽  
Pka Value ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Benzofuranone is a sort of important skeleton in many fields, such as natural products, pharmaceuticals, building blocks, antioxidants and dyes. Their efficient synthesis and transformations have attracted great attentions in organic synthesis. They can be synthesized by Friedel−Crafts reaction, intramolecular dehydration ring-closing reaction and transition-metal-catalyzed reaction, etc. And their direct utilization to prepare other functional molecules enhances their further application. Due to their low pKa value and easy enolization ability, the transformation of benzofuranones via C(3)-H bond functionalization is a hot issue in the last ten years. Herein, we highlight the advances on the synthesis of benzofuranones and its transformation via C-H functionalization. Some of other transformations related to benzofuranones are also referred in this review.

scholarly journals Photo-induced copper-catalyzed sequential 1,n-HAT enabling the formation of cyclobutanols

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Zhusong Cao ◽  
Jianye Li ◽  
Guozhu Zhang
Keyword(s):  
Natural Products ◽  
Hydrogen Atom ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Copper Complex ◽  
Building Blocks ◽  
Hydrogen Atom Transfer ◽  
Efficient Synthesis ◽  
Bond Functionalization ◽  
Cascade Cyclization

AbstractCyclobutanols are privileged cyclic skeletons in natural products and synthetic building blocks. C(sp3)−H functionalization is a prolonged challenge in organic synthesis. The synthesis of cyclobutanols through double C(sp3)-H bond functionalization remains elusive. Here we report the efficient synthesis of cyclobutanols through intermolecular radical [3 + 1] cascade cyclization, involving the functionalization of two C − H bonds through sequential hydrogen atom transfer. The copper complex reduces the iodomethylsilyl alcohols efficiently under blue-light irradiation to initiate the tandem transformation. The mild reaction tolerates a broad range of functional groups and allows for the facile generation of elaborate polycyclic structures.

Recent Advances of Sulfonylation Reactions in Water

2020 ◽  
Vol 17 (4) ◽  
pp. 271-281
Author(s):  
Li Wu ◽  
Lifen Peng ◽  
Zhifang Hu ◽  
Yinchun Jiao ◽  
Zilong Tang
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Low Cost ◽  
Point Of View ◽  
Sulfinic Acid ◽  
Sulfonyl Chlorides ◽  
Recent Advances ◽  
Water As Solvent ◽  
Proton Source ◽  
Sulfinic Acids

Background: The sulfonyl groups are general structural moieties present in agrochemicals, pharmaceuticals, and natural products. Recently, many efforts have been focused on developing efficient procedures for preparation of organic sulfones. Materials and Methods: Water, a proton source, is considered one of the most ideal and promising solvents in organic synthesis for its easy availability, low cost, nontoxic and nonflammable characteristics. From the green and sustainable point of view, more and more reactions are designed proceeding in water. Objective: The review focuses on recent advances of sulfonylation reactions proceeding in water. Sulfonylation reactions using sodium sulfinates, sulfonyl hydrazides, sulfinic acids, and sulfonyl chlorides as sulfonating agents were introduced in detail. Results and Discussion: In this review, sulfonylation reactions proceeding in water developed in recent four yields were presented. Sulfonylation reactions using water as solvent have attracted more and more attention because water is one of the most ideal and promising solvents in organic synthesis for its facile availability, low cost, nontoxic and nonflammable properties. Conclusion: Numerous sulfonating agents such as sodium sulfinates, sulfonyl hydrazides, sulfinic acid, sulfonyl chlorides and disulfides are efficient for sulfonylation reactions which proceed in water.

Metal and Non-Metal Catalysts in the Synthesis of Five-Membered S-Heterocycles

2019 ◽  
Vol 16 (2) ◽  
pp. 258-275 ◽  
Author(s):  
Navjeet Kaur
Keyword(s):  
Organic Synthesis ◽  
Biological Activities ◽  
Reaction Times ◽  
Research Field ◽  
Environmentally Benign ◽  
Metal Catalyst ◽  
Efficient Synthesis ◽  
Heterocyclic Molecules ◽  
The Past ◽  
Harsh Conditions

Background:A wide variety of biological activities are exhibited by N, O and S containing heterocycles and recently, many reports appeared for the synthesis of these heterocycles. The synthesis of heterocycles with the help of metal and non-metal catalyst has become a highly rewarding and important method in organic synthesis. This review article concentrated on the synthesis of S-heterocylces in the presence of metal and non-metal catalyst. The synthesis of five-membered S-heterocycles is described here.Objective:There is a need for the development of rapid, efficient and versatile strategy for the synthesis of heterocyclic rings. Metal, non-metal and organocatalysis involving methods have gained prominence because traditional conditions have disadvantages such as long reaction times, harsh conditions and limited substrate scope.Conclusion:The metal-, non-metal-, and organocatalyst assisted organic synthesis is a highly dynamic research field. For ßthe chemoselective and efficient synthesis of heterocyclic molecules, this protocol has emerged as a powerful route. Various methodologies in the past few years have been pointed out to pursue more sustainable, efficient and environmentally benign procedures and products. Among these processes, the development of new protocols (catalysis), which avoided the use of toxic reagents, are the focus of intense research.

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