Tandem Condensation/Rearrangement Reaction of 2‐Aminohetarene <i>N</i>‐Oxides for the Synthesis of Hetaryl Carbamates

Bystrov, Dmitry M.; Zhilin, Egor S.; Ферштат, Леонид Л.; Romanova, Anna A.; Ananyev, Ivan V.; Махова, Нина Н.

doi:10.1002/adsc.201800407

Cited by 20 publications

(5 citation statements)

References 59 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The second to last step was the preparation of the amide oximes 18, 19 and 20 by the reaction of the cyano group of 15, 16 and 17 with hydroxylamine hydrochloride. Refluxing 18, 19 and 20 in 2N NaOH overnight gave the desired 3-and 4-substituted 3-aminofurazans 6, 7 and 8 by intramolecular ring closure [15][16][17]. For the preparation of the 3-amino-4-(4-nitrophenyl)-1,2,5-oxadiazole 21, a slightly different reaction scheme starting from phenylacetonitrile was applied.…”

Section: Chemistrymentioning

confidence: 99%

Structure–Activity Relationships and Antiplasmodial Potencies of Novel 3,4-Disubstituted 1,2,5-Oxadiazoles

Hochegger,

Hermann,

Dolensky

et al. 2023

IJMS

View full text Add to dashboard Cite

The 4-substituted 3-amino-1,2,5-oxadiazole 1 from the Malaria Box Project of the Medicines for Malaria Venture foundation shows very promising selectivity and in vitro activity against Plasmodium falciparum. Within the first series of new compounds, various 3-acylamino analogs were prepared. This paper now focuses on the investigation of the importance of the aromatic substituent in ring position 4. A number of new structure–activity relationships were elaborated, showing that antiplasmodial activity and selectivity strongly depend on the substitution pattern of the 4-phenyl moiety. In addition, physicochemical parameters relevant for drug development were calculated (logP and ligand efficiency) or determined experimentally (CYP3A4-inhibition and aqueous solubility). N-[4-(3-ethoxy-4-methoxyphenyl)-1,2,5-oxadiazol-3-yl]-3-methylbenzamide 51 showed high in vitro activity against the chloroquine-sensitive strain NF54 of P. falciparum (PfNF54 IC50 = 0.034 µM), resulting in a very promising selectivity index of 1526.

show abstract

Section: Chemistrymentioning

confidence: 99%

Structure–Activity Relationships and Antiplasmodial Potencies of Novel 3,4-Disubstituted 1,2,5-Oxadiazoles

Hochegger,

Hermann,

Dolensky

et al. 2023

IJMS

View full text Add to dashboard Cite

show abstract

“…Makhova's group recently described the BF 3 ‐catalyzed preparation of hetaryl carbamates 392 by condensation of 2‐aminohetarene N ‐oxide 391 with trimethyl orthoformate followed by intramolecular N ‐oxide oxygen transfer (Scheme 114). [149] …”

Section: Functionalization At C2‐benzylic Position Of Pyridine/quinolmentioning

confidence: 99%

Recent Advances in the Synthesis of C2‐Functionalized Pyridines and Quinolines Using N‐Oxide Chemistry

et al. 2020

View full text Add to dashboard Cite

While remarkable progress has recently been made for the direct C−H‐functionalization of azines, its application is still limited by a lack of accessible functional groups (primarily carbon‐based) and poor regioselectivity. In contrast, C2‐functionalized pyridines and quinolines can be easily synthesized by treating readily available N‐oxides with various reagents under appropriate activation conditions. This review seeks to comprehensively document the available synthetic methods for introducing functional groups at the C2 position of pyridines and quinolines. In this work, we highlight recent developments in the C2‐functionalization of pyridine and quinoline N‐oxides and address both the mechanisms and regioselectivity of the reactions. We also describe the pathways and reactive species involved in these processes and highlight a number of medically relevant nitrogen heteroaromatics.

show abstract

“…A novel reactivity mode of 3-aminofuroxans 49 was also recently established. 53 A scope of the Bystrov-Zhilin-Fershtat rearrangement was further extended on the Sc(OTf)3-catalyzed condensation of aminofuroxanyl amidoxime 54 with aldehydes. Amidoxime functionality was annulated to the 1,2,4-oxadiazole ring, while 4-aminofuroxan moiety was converted to the (carbamoyl)furazan one.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…A novel reactivity mode of 3-aminofuroxans 49 was also established recently. 53 Compounds 49 were converted into the corresponding imino ethers 50, which were found to participate in a cyanide-catalyzed intramolecular rearrangement into furazanyl carbamates 51 (we propose naming this reaction as the Bystrov-Zhilin-Fershtat rearrangement). A plausible mechanism for the Bystrov-Zhilin-Fershtat rearrangement includes nucleophilic addition of the cyanide anion to the C(sp 2 ) atom of the imino ether functionality.…”

Section: Short Review Synthesismentioning

confidence: 99%

Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity

Ферштат

Teslenko

2021

Synthesis

Self Cite

View full text Add to dashboard Cite

Five-membered heterocyclic N-oxides attracted special attention due to their strong application potential in medicinal chemistry and advanced materials science. In this regard, novel methods for their synthesis and functionalization are constantly required. In this short review, recent state-of-the-art achievements in the chemistry of isoxazoline N-oxides, 1,2,3-triazole 1-oxides and 1,2,5-oxadiazole 2-oxides are briefly summarized. Main routes to transition-metal-catalyzed and metal-free functionalization protocols along with mechanistic considerations are outlined. Transformation patterns of the hetarene N-oxide rings as precursors to other nitrogen heterocyclic systems are also presented.

show abstract

Tandem Condensation/Rearrangement Reaction of 2‐Aminohetarene N‐Oxides for the Synthesis of Hetaryl Carbamates

Cited by 20 publications

References 59 publications

Structure–Activity Relationships and Antiplasmodial Potencies of Novel 3,4-Disubstituted 1,2,5-Oxadiazoles

Structure–Activity Relationships and Antiplasmodial Potencies of Novel 3,4-Disubstituted 1,2,5-Oxadiazoles

Recent Advances in the Synthesis of C2‐Functionalized Pyridines and Quinolines Using N‐Oxide Chemistry

Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity

Contact Info

Product

Resources

About