4.0 Article

Efficient Construction of Azaspiro[4.5]trienone Libraries via Tandem Ugi 4CC/Electrophilic ipso-Iodocyclization in One-Pot

期刊

ACS COMBINATORIAL SCIENCE
卷 17, 期 8, 页码 474-481

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acscombsci.5b00065

关键词

multicomponent reaction (MCR); Ugi reaction; U4CC; ipso-iodocyclization; Suzuki coupling; Spiro compounds

资金

  1. CSIR, New Delhi under THUNDER [BSC-0102]
  2. CSIR, New Delhi under ACT [CSC0301]
  3. UGC, New Delhi

向作者/读者索取更多资源

A solution-phase parallel synthesis of pharmaceutically important azaspiro[4.5]trienones has been developed by performing tandem Ugi four-component condensation (U4CC), involving substituted p-anisidines, aldehydes, 3-alkyl/aryl-propiolic acids, and isocyanides, and iodine-mediated ipso-iodocyclization in one-pot. This highly atom economical process produced functionalized azaspiro[4.5]trienones in good to excellent overall yields and products were easily isolated by precipitation followed by crystallization. These vinyl-iodide bearing azaspiro[4.5]trienones were utilized for further modifications through Suzuki coupling and deiodination reaction to demonstrate the suitability of these products for various palladium catalyzed modifications. The present method provides an easy access to highly functionalized azaspiro[4.5]trienones that can be useful in drug discovery research.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.0
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Review Chemistry, Multidisciplinary

A Comparative Synthetic Strategy Perspective on α-Amino Acid- and Non-Amino Acid-Derived Synthons towards Total Syntheses of Selected Natural Macrolides

Srinivas Lavanya Kumar Manda, Shashank Tripathi, Anirban Ghoshal, Mayur D. Ambule, Ajay Kumar Srivastava, Gautam Panda

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Chemistry, Organic

Construction of Highly Functionalized Piperazinones via Post-Ugi Cyclization and Diastereoselective Nucleophilic Addition

Shashank Tripathi, Mayur D. Ambule, Ajay Kumar Srivastava

JOURNAL OF ORGANIC CHEMISTRY (2020)

Review Chemistry, Organic

Advances in Base-Mediated Post-Ugi Transformations via Peptidyl Anion Trapping

Anirban Ghoshal, Mayur D. Ambule, Anamika Yadav, Ajay Kumar Srivastava

Summary: This mini-review discusses the advances in base-mediated post-Ugi transformations, focusing on the abstraction of an alpha proton adjacent to amide carbonyl in aldehyde-derived Ugi adducts under basic conditions for intramolecular and intermolecular cyclizations. The methodologies are classified based on the peptidyl anion trapping under various reaction conditions, highlighting their importance in synthetic and medicinal chemistry.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Infectious Diseases

Phase III, Randomized, Double-blind, Placebo controlled trial of Efficacy, Safety and Tolerability of Antiviral drug Umifenovir vs Standard care of therapy in non-severe COVID-19 patients

Ravishankar Ramachandran, Vivek Bhosale, Himanshu Reddy, Virendra Atam, M. M. A. Faridi, Jalees Fatima, Vaibhav Shukla, Zaw A. Khan, Hana Khan, Vikram Singh, Mahendra Pal Singh Negi, Mukesh Srivastava, Ajay Kumar Srivastava, Chandra Bhushan Tripathi, Nayan Ghosh, Nilanjana Majumdar, Raj Kamal Tripathi, Srikanta Kumar Rath, Prabhat Ranjan Mishra, Sharad Sharma, Tapas K. Kundu

Summary: Umifenovir shows efficacy, safety and tolerability in non-severe COVID-19 adult patients. It meets the primary and secondary endpoint criteria and exhibits statistically significant efficacy in mild-asymptomatic patients. It is efficacious, safe and well-tolerated at the tested dosage of 800mg BID, maximum 14 days.

INTERNATIONAL JOURNAL OF INFECTIOUS DISEASES (2022)

Article Biophysics

Nanoglycocluster based diagnostic platform for colorimetric detection of bacteria; A comparative study analysing the effect of AuNPs size, linker length, and glycan diversity

Nitesh Priyadarshi, Mayur D. Ambule, Shimayali Kaushal, Asheesh Kumar, Poonam Sagar, Ajay Kumar Srivastava, Nitin Kumar Singhal

Summary: Nanoglycoclusters, a type of functional nanomaterial, have various applications such as detection, imaging, and targeting of bacteria. By controlling the size of gold nanoparticles, the length of linker molecules, and the density of glycans, selective detection of specific bacteria and lectins can be achieved.

BIOSENSORS & BIOELECTRONICS (2022)

Article Chemistry, Organic

Copper-Catalyzed Oxidative [3+2]-Annulation of Quinoxalin2(1H)-one with Oxime Esters toward Functionalized Pyrazolo[1,5-a]quinoxalin-4(5H)-ones as Opioid Receptor Modulators

Anamika Yadav, Anubhav Yadav, Shashank Tripathi, Varun Dewaker, Ruchir Kant, Prem Narayan Yadav, Ajay Kumar Srivastava

Summary: Novel Pyrazolo[1,5-a]quinoxalin-4(5H)-one derivatives, acting as opioid receptor modulators, have been synthesized through a copper-catalyzed reaction. The synthesized compounds showed antagonistic effects on opioid receptors, and docking studies confirmed their binding with hKOR protein.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

Regioselective Synthesis of Functionalized Pyrrolo[1,2-a]pyrazine-3,6(2H,4H)-diones via Tandem Post-Ugi Cyclization and Gold(I)- Catalyzed Annulation

Sangh Priya Singh, Asheesh Kumar, Ruchir Kant, Ajay Kumar Srivastava

Summary: A convenient method for the synthesis of less explored pyrrolo[1,2-a]pyrazine-3,6(2H,4H)-diones from Ugi adducts is described. The method involves acid-mediated cyclization of Ugi adducts to form dihydropyrazinones followed by gold(I)-catalyzed regioselective annulation. By reacting various substituted dihydropyrazinones under optimized conditions, densely functionalized pyrrolo[1,2-a]pyrazine-3,6(2H,4H)-diones were obtained in good-to-excellent yields. It was also observed that some acetone-derived Ugi adducts produced 7-acyl-pyrroloimidazolones as byproducts during TFA-mediated cyclization.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

Stereodivergent Synthesis of (Z)-/(E)-β-Sulfonylacrylamides via Tandem Difunctionalization of Alkynes with Sulfinates and Isocyanides

Shashank Tripathi, Monty Kumar, Mayur D. Ambule, Ankit Saxena, Ruchir Kant, Sanjeev K. Shukla, Ajay Kumar Srivastava

Summary: Stereoselective difunctionalizations of alkynes were achieved to prepare (Z)-/(E)-fi-sulfonylacrylamides. The (Z)-fi-sulfonylacrylamides were generated via a one-pot process, while the (E)-fi-sulfonylacrylamides were prepared in a two-step synthesis.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Synthesis of Azaspiro Tricyclic Scaffolds through Post-Ugi Modifications: Scope and Limitation of Aza-Michael Cyclization

Mayur D. Ambule, Mandweep Bhumij, Asheesh Kumar, Ruchir Kant, Ajay Kumar Srivastava

Summary: Post-Ugi modifications provide an atom-economic approach to construct functionalized heterocycles. In this study, we demonstrated the synthesis of highly functionalized azaspiro tricyclic scaffolds through Ugi condensation, ipso-cyclization, and aza-Michael ring closures. We also investigated the substrate scope and limitations of aza-Michael cyclizations and developed new methods for the preparation of novel azaspiro tricyclic scaffolds.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Chemistry, Organic

Regioselective Synthesis of Phenanthridines via Pd(II)-Catalyzed Annulative C(sp 2)-H Activation

Anamika Yadav, Surabhi Upadhyay, Ruchir Kant, Ajay Kumar Srivastava

Summary: A robust synthesis of phenanthridines has been achieved via Pd(II)-catalyzed domino C(sp(2))-H activation/N-arylation using oxime esters with aryl acyl peroxides in a highly regioselective manner. This method is compatible with various oxime esters derived from acetophenone and benzophenone, allowing modular construction of functionalized phenanthridines with wide electronic functionality tolerance.

JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Chemistry, Organic

Palladium(II)-Catalyzed Decarboxylative Difunctionalization of Alkynoic Acids To Access (E)-β-Sulfonylacrylamides and DFT Study

Shashank Tripathi, Monty Kumar, Ayush Shivhare, Ruchir Kant, Milind M. Deshmukh, Ajay Kumar Srivastava

Summary: In this study, a palladium(II)-catalyzed regio- and stereoselective difunctionalization of alkynoic acids was successfully achieved using sodium sulfinates and isocyanides to synthesize (E)-ss-sulfonylacrylamides. The reaction showed good functional group tolerance and excellent regio- and stereoselectivity on aromatic, heteroaromatic, and aliphatic alkynoic acids. DFT calculations were performed to elucidate the reaction mechanism and the stereoselective formation of (E)-ss-sulfonylacrylamides.

ORGANIC LETTERS (2023)

Article Chemistry, Multidisciplinary

Synthesis of β- and γ-lactam fused dihydropyrazinones from Ugi adductsviaa sequential ring construction strategy

Sangh Priya Singh, Shashank Tripathi, Anamika Yadav, Ruchir Kant, Hemant Kumar Srivastava, Ajay Kumar Srivastava

CHEMICAL COMMUNICATIONS (2020)

Article Chemistry, Organic

Silver/Palladium Relay Catalyzed Cross-Coupling ofN'-Acetyl-8-quinolinesulfonylhydrazide with Alcohols: An Easy Access to 8-Quinolinesulfinate Esters

Anamika Yadav, Mayur D. Ambule, Ruchir Kant, Ajay K. Srivastava

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Copper-catalyzed oxidative cleavage of Passerini and Ugi adducts in basic medium yielding α-ketoamides

Anirban Ghoshal, Mayur D. Ambule, Revoju Sravanthi, Mohit Taneja, Ajay Kumar Srivastava

NEW JOURNAL OF CHEMISTRY (2019)

暂无数据