A highly efficient, clean, and simple procedure for the synthesis of a privilege imidazo[4,5-b]pyridine scaffold from 2-chloro-3-nitropyridine in combination with environmentally benign H2O-IPA as a green solvent is presented. The scope of the novel method has been demonstrated through the tandem sequence of SNAr reaction with substituted primary amines followed by the in situ nitro group reduction and subsequent heteroannulation with substituted aromatic aldehydes to obtain functionalized imidazo[4,5-b]pyridines with only one chromatographic purification step. The synthesis pathway appears to be green, simple, and superior compared with other already reported procedures, with the high abundance of reagents and great ability in expanding the structural diversity. © 2018 American Chemical Society.

Kaushik Chanda

Department of Chemistry

School of Advanced Sciences

Vellore Campus

Padmaja R.D

Devi C.V

Mukku N

Maiti B.

Fulltext

Vellore Institute of Technology (VIT) is a private university located in&nbsp;Tamil Nadu, India. Founded in 1984, as Vellore Engineering College, the institution offers 20 undergraduate, 34 postgraduate, four integrated and four research programs. It has campuses in Vellore, Amravati, Bhopal and Chennai.

VIT is one of the top ranked private universities in India according to NIRF, THE and QS Rankings.&nbsp;Govt. of India has recognized&nbsp;VIT, Vellore as an&nbsp;Institution of Eminence. This has allowed VIT to take independent quality initiatives and move up in world ranking.

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VIT University

ACS Omega

A highly efficient unprecedented catalyst-free microwave-assisted procedure for synthesizing benzo[d]imidazo[2,1-b]thiazoles and N -alkylated 2-aminobenzo[d]oxazol in green media was developed.

RSC Advances

On water catalyst-free synthesis of benzo[d]imidazo[2,1-b] thiazoles and novel N-alkylated 2-aminobenzo[d]oxazoles under microwave irradiation

Simultaneous C−N, and N−N bond-forming methods for one-pot transformations are highly challenging in synthetic organic chemistry. In this study, the Cu2O rhombic dodecahedra-catalyzed synthesis of 2H-indazoles is demonstrated with good to excellent yields from readily available chemicals. This one-pot procedure involves Cu2O nanoparticle-catalyzed consecutive C−N, and N−N bond formation followed by cyclization to yield 2H-indazoles with broad substrate scope and high functional group tolerance. Various cell-based bioassay studies demonstrated that 2H-indazoles inhibit the growth of cancer cells, typically through induction of apoptosis in a dose-dependent manner. Moreover, 2H-indazoles tested in the MDA-MB-468 cell line were capable of inhibiting cancer cell migration and invasion. Thus, it is shown that 2H-indazoles have potent in vitro anticancer activity that warrant further investigation of this compound class.

ChemMedChem

Assembly of Fully Substituted 2H-Indazoles Catalyzed by Cu2O Rhombic Dodecahedra and Evaluation of Anticancer Activity

Rapid Construction of an Imidazo[4,5-b]pyridine Skeleton from 2-Chloro-3-nitropyridine via Tandem Reaction in H2O-IPA Medium

Indole-based alkaloids are well-known in the literature for their diverse biological properties. Polysubstituted optically active tetrahydro-β-carboline derivatives functionalized on C-1 position are the common structural motif in most of the indole-based alkaloids, as well as highly marketed drugs. The stereoselective Pictet-Spengler reaction is one of the currently most important synthetic techniques used for the preparation of these privileged tetrahydro-β-carboline scaffolds. To date, there are numerous research reports that have been published on the synthesis of the tetrahydro-β-carboline scaffold both on solid phase, as well as in solution phase. Moreover rapid growth has been observed for the enantioselective synthesis of tetrahydro-β-carboline scaffold using chiral organocatalysts. In this Review, efforts have been taken to shed light on the latest information available on different strategies to synthesize tetrahydro-β-carboline both on solid phase and in solution phase during the last 20 years. Furthermore, we believe that the present synthetic methodologies covered in this Review will help to improve the status of this privileged tetrahydro-β-carboline scaffold in its use for drug discovery. © 2017 American Chemical Society.

ACS Combinatorial Science

Application of Pictet–Spengler Reaction to Indole-Based Alkaloids Containing Tetrahydro-β-carboline Scaffold in Combinatorial Chemistry

ChemSusChem

2-Methyltetrahydrofuran: A Green Solvent for Iron-Catalyzed Cross-Coupling Reactions

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§ 129 Geschäftsordnung; Verzeichnis der Teilnehmer

Drug Testing and Analysis

Sensitivity of GC-EI/MS, GC-EI/MS/MS, LC-ESI/MS/MS, LC-Ag+CIS/MS/MS, and GC-ESI/MS/MS for analysis of anabolic steroids in doping control

Journal	Data powered by TypesetACS Omega
Publisher	Data powered by TypesetAmerican Chemical Society (ACS)
ISSN	2470-1343
Open Access	Yes