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

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.

Download Full-text

Recent advances in the synthesis of oxaspirolactones and their application in the total synthesis of related natural products

Organic & Biomolecular Chemistry ◽

10.1039/c9ob01212e ◽

2019 ◽

Vol 17 (31) ◽

pp. 7270-7292 ◽

Cited By ~ 7

Author(s):

Sagar S. Thorat ◽

Ravindar Kontham

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Natural Product ◽

Medicinal Chemistry ◽

Natural Product Chemistry ◽

Structural Motifs ◽

Recent Advances ◽

Synthetic Molecules ◽

Product Chemistry

Oxaspirolactones are ubiquitous structural motifs found in natural products and synthetic molecules with a diverse biochemical and physicochemical profile, and represent a valuable target in natural product chemistry and medicinal chemistry.

Download Full-text

Recent Advances in the Chemistry of 2-Acylaziridines

Synthesis ◽

10.1055/s-0036-1590889 ◽

2017 ◽

Vol 49 (23) ◽

pp. 5093-5104 ◽

Cited By ~ 5

Author(s):

Alena Pankova ◽

Mikhail Kuznetsov

Keyword(s):

Carbonyl Group ◽

Ring Opening ◽

Bond Cleavage ◽

Aziridine Ring ◽

Reaction Selectivity ◽

Recent Advances ◽

Nitrogen Containing Compounds

This review highlights recent achievements in the transformations of 2-acylaziridines toward the synthesis of cyclic and acyclic nitrogen-containing compounds. The influence of a carbonyl group on reaction selectivity is discussed.1 Introduction2 Reactions via C–C Bond Cleavage3 Reactions via C–N Bond Cleavage3.1 Reactions Starting with the Aziridine Ring Opening3.2 Reactions Starting at the Carbonyl Group4 Conclusion

Download Full-text

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

Organic & Biomolecular Chemistry ◽

10.1039/d0ob00777c ◽

2020 ◽

Vol 18 (25) ◽

pp. 4692-4708 ◽

Cited By ~ 1

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.

Download Full-text

Recent Advances in Cycloaddition Reactions with Alkynes to Construct Heterocycles

Synthesis ◽

10.1055/s-0040-1707355 ◽

2020 ◽

Vol 52 (24) ◽

pp. 3818-3836

Author(s):

Jin-Heng Li ◽

De-Lie An ◽

Jing-Hao Qin

Keyword(s):

Natural Products ◽

Transition Metal ◽

Heterocyclic Compounds ◽

Cycloaddition Reactions ◽

Structural Motifs ◽

Recent Advances ◽

Wide Range ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

Heterocyclic compounds, especially N-heterocycles and O-heterocycles, are prominent structural motifs present in numerous natural products and medically and/or economically important compounds. This review aims to describe the development of transition-metal-catalyzed cycloaddition reactions of functionalized m-atom partners with alkynes to access a wide range of five-, six-, and seven-membered heterocycles, that is functionalized N-heterocycles and O-heterocycles such as azepines, isoquinolines, isocoumarins, spiroheterocycles, indoles, furans, and pyrroles, in a selectively controlled manner with an emphasis on scope and limitations and with a discussion of the mechanisms.1 Introduction2 Intermolecular Cycloaddition To Construct Azepine Derivatives2.1 [5+2] Cycloaddition2.2 [3+2+2] Cycloaddition2.3 [3+2]/[5+2] Cycloaddition3 Intermolecular [4+2] Cycloaddition To Construct Isoquinolines or Isocoumarins4 Intermolecular [3+2] Cycloaddition To Construct Spiroheterocyclic Compounds, Indoles, Furans, and Pyrroles5 Summary and Outlook

Download Full-text

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

Catalysis Science & Technology ◽

10.1039/d1cy01438b ◽

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...

Download Full-text

Recent Advances in Therapeutic Applications of Bisbenzimidazoles

Medicinal Chemistry ◽

10.2174/1573406415666190416120801 ◽

2020 ◽

Vol 16 (4) ◽

pp. 454-486 ◽

Cited By ~ 2

Author(s):

Smita Verma ◽

Vishnuvardh Ravichandiran ◽

Nihar Ranjan ◽

Swaran J.S. Flora

Keyword(s):

Heterocyclic Compounds ◽

Wide Spectrum ◽

Dna Recognition ◽

Present Review ◽

Pharmacological Activities ◽

Structural Motifs ◽

Therapeutic Applications ◽

The Past ◽

Recent Advances

Nitrogen-containing heterocycles are one of the most common structural motifs in approximately 80% of the marketed drugs. Of these, benzimidazoles analogues are known to elicit a wide spectrum of pharmaceutical activities such as anticancer, antibacterial, antiparasitic, antiviral, antifungal as well as chemosensor effect. Based on the benzimidazole core fused heterocyclic compounds, crescent-shaped bisbenzimidazoles were developed which provided an early breakthrough in the sequence-specific DNA recognition. Over the years, a number of functional variations in the bisbenzimidazole core have led to the emergence of their unique properties and established them as versatile ligands against several classes of pathogens. The present review provides an overview of diverse pharmacological activities of the bisbenzimidazole analogues in the past decade with a brief account of its development through the years.

Download Full-text

Synthesis of Polycycles and Oxacycles by Tandem Metathesis of endo–norbornene Derivatives

Synthesis ◽

10.1055/a-1348-4242 ◽

2021 ◽

Author(s):

Sambasivarao Kotha ◽

Sunil Pulletikurti ◽

Ambareen Fatma ◽

gopal dhangar ◽

gonna somu Naidu

Keyword(s):

Natural Products ◽

Metal Complex ◽

Carbonyl Group ◽

Single Step ◽

Time Dependent ◽

Computational Studies ◽

Nmr Studies ◽

Tricyclic Compounds ◽

One Step ◽

Norbornene Derivatives

Here, we have demonstrated that the presence of a carbonyl group at C7 position is preventing the olefin metathesis of endo-norbornene derivatives due to the complexation of the metal alkylidene. Time-dependent NMR studies showed the presence of new proton signals in the metal alkylidene region, which indicate the formation of metal complex with the carbonyl group of the substrate. These observations were further proved by ESI-MS analysis. Whereas, computational studies provided that the catalyst was interacting with the C7 carbonyl group and aligned perpendicular to that of norbornene olefin. Later, these endo-keto norbornene derivatives were reduced to hydroxyl derivatives diastereoselectively. Ring-rearrangement metathesis (RRM) of these hydroxyl derivatives, produced the [6/5/6], and [5/6/5] carbo-tricyclic cores of the natural products in one step. Whereas the RRM of O-allyl derivatives, delivered the oxa-tricyclic compounds in a single step with excellent yields.

Download Full-text