Tunable Zinc-Mediated Reductive Cyclization of Diastereomeric 3-Nitro-4-phenacyl-2-(trihalomethyl)chromanes to Fused Pyrroline N-Oxides, Pyrrolines, and Pyrrolidines DOI
Vladislav Yu. Korotaev, Igor B. Kutyashev,

Maxim S. Sannikov

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1567 - 1590

Published: Jan. 20, 2024

Reductive cyclization of trans,trans- and trans,cis-isomers the 2-CF3-substituted 3-nitro-4-phenacylchromanes with Zn-based reductive systems, depending on conditions, affords 4-CF3-substituted 1,3a,4,9b-tetrahydrochromeno[3,4-b]pyrrole 3-oxides, 1,3a,4,9b-tetrahydrochromeno[3,4-b]pyrroles, or 1,2,3,3a,4,9b-hexahydrochromeno[3,4-b]pyrroles in good yields without changing relative configuration pyran ring. A similar process involving 2-CCl3-substituted is accompanied by dehalogenation to form corresponding 4-dichloromethyl-substituted fused chromanes along 3-(2-hydroxyaryl)-2-(2,2-dichlorovinyl)-5-phenyl-2H-pyrroline 1-oxides as ring opening products. The structure obtained products was reliably confirmed X-ray diffraction analysis 2D NMR spectroscopy.

Language: Английский

Base catalyzed one-pot thia-Michael addition-oxidation reaction of hetero-aromatic thiols to 2-aryl-3-nitro-2H-chromenes and their antibacterial evaluation DOI
Barsha Samanta, Bhabani Shankar Panda, Seetaram Mohapatra

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(11), P. 4953 - 4959

Published: Jan. 1, 2024

A thia-Michael addition reaction was developed for the synthesis of heteroaromatic thiol-based 2 H -chromenes and antibacterial activity studied against two pathogenic bacterial strains, E. coli , S. aureus .

Language: Английский

Citations

6
Current Developments in Michael Addition Reaction using Heterocycles as Convenient Michael Donors DOI
Barsha Samanta, Bhabani Shankar Panda, Seetaram Mohapatra

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: July 3, 2024

Abstract The Michael addition reaction, a cornerstone of contemporary organic synthesis, has witnessed resurgence interest owing to its ability forge intricate carbon‐carbon and carbon‐heteroatom bonds. In the past few years, heterocyclic compounds have been rigorously used as donors, their architectural diversity distinct reactivity with or without presence base/transition metals/organocatalysts. This review encapsulates latest breakthroughs in chemistry involving reaction using donors. It delivers comprehensive update on developments triggered by potent heterocycles since 2017, highlighting novel innovative methodologies, strategic insights.

Language: Английский

Citations

3
Divergent Behavior of β‐Carbonyl‐Substituted 1H‐Benzo[f]chromenes Under Henry Reaction Conditions DOI Open Access
Кирилл С. Корженко, Dmitry V. Osipov,

Alexandra S. Chechulina

et al.

Asian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 5, 2025

Abstract A series of β‐carbonyl‐substituted 1 H ‐benzo[ f ]chromenes has been introduced into the reaction with nitromethane in presence ammonium acetate. It shown that case ]chromene‐2‐carbaldehydes, does not stop at formation classical Henry products − β‐nitroalcohols, but their dehydration to nitrovinylchromenes takes place. In alkyl(benzochromen‐2‐yl)ketones, 3‐alkyl‐2‐(2‐nitrovinyl)‐1 are formed, and methoxalyl‐substituted benzochromenes give 10‐amino‐7a,8‐dihydrobenzo[5,6]chromeno[2,3‐ b ]pyrrol‐9(11 )‐ones under conditions.

Language: Английский

Citations

0
Regio- and chemoselective synthesis of flavanone isosteres via multicomponent reactions: synergistic role of hydrogen bonding and solvent effects DOI
Lixin Zhang,

Ziyi Tang,

Xinyue Liu

et al.

Molecular Diversity, Journal Year: 2025, Volume and Issue: unknown

Published: March 26, 2025

Language: Английский

Citations

0
Design and synthesis of tetrahydrochromeno[3,4-e]isoindole-1,3(2H,3aH)-dione derivatives via the Diels–Alder reaction: molecular docking, antibacterial activity, ADMET analysis and photophysical properties DOI Creative Commons

Sonali Priyadarshini Parida,

Seetaram Mohapatra,

Suhasini Mohapatra

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(18), P. 14499 - 14517

Published: Jan. 1, 2025

A series of fused tetrahydrochromeno isoindole dione derivatives was successfully synthesized. In silico physicochemical, pharmacokinetic, and ADMET, UV-visible fluorescence study all synthesized compound has been carried out.

Language: Английский

Citations

0
Divergent Transformations of 2-Nitro-1H-benzo[f]chromenes in Reactions with Alkylidenemalononitriles: Access to Naphtho[2,1-b]furans via Base-Mediated Pyran Ring Contraction DOI
Кирилл С. Корженко,

Anastasiya S. Yushkova,

Dmitry V. Osipov

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1310 - 1315

Published: Feb. 8, 2024

The action of 2-(1-arylethylidene)malononitriles on 2-nitro-1H-benzo[f]chromenes in the presence Et3N and MoO3·2H2O results naphtho[2,1-b]furans containing an allylidenemalononitrile unit α-position. reaction proceeds with contraction pyran ring via a cascade carba-Michael addition/retro-oxa-Michael reaction/tautomerization/SN2/oxidation process. In contrast, cyclic Knoevenagel adduct derived from 1-indanone malononitrile leads to dihydroindeno[1,2-c]xanthenes. possibility further transformations naphtho[2,1-b]furan derivatives as useful precursors their optical properties were also investigated.

Language: Английский

Citations

2
Kinetic Resolution of a Planar–Chiral [2.2]Paracyclophane via Michael Addition to Nitroolefins Catalyzed by N‐Terminal Guanidinylated Helical Peptide DOI Creative Commons

Jiaqi Tian,

Kenya Tamaribuchi,

Isao Yoshikawa

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(16)

Published: Feb. 27, 2024

Abstract Kinetic resolution of 4‐(2‐nitrovinyl)[2.2]paracyclophane based on N‐terminal–guanidinylated resin–bound helical peptide catalyzed asymmetric Michael addition malonate esters was developed. This approach provides a new pathway to enantiopure paracyclophane derivatives characterized by both planar and central chirality, along with the recovery chiral substrate selectivity factor up 111. Additionally, synthetic potential resulting products has been showcased through their successful transformation into β‐substituted γ‐aminobutyric acid.

Language: Английский

Citations

2
Domino Conjugate Addition-1,4-Aryl Migration for the Synthesis of α,β-Difunctionalized Amides DOI Creative Commons
Haoqi Zhang, Yi Xiao, Miran Lemmerer

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(7), P. 2456 - 2461

Published: June 17, 2024

A domino difunctionalization of sulfonyl(acryl)imides to form β-substituted α-aryl amides is reported. This transformation involves a 1,4-addition followed by polar Truce-Smiles rearrangement process, entropically driven release SO

Language: Английский

Citations

2
Synthesis of Highly Substituted 1,2,4-Triazole-Based 3-Nitrochromanes through Aza-Michael Addition Reaction under Catalyst- and Base-Free Conditions DOI
Seetaram Mohapatra,

Tapaswini Das,

Sonali Priyadarshini Parida

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 56(01), P. 151 - 160

Published: Oct. 18, 2023

Abstract A simple and efficient aza-Michael addition reaction of 1,2,4-triazoles to functionalized 2-aryl-3-nitro-2H-chromenes has been demonstrated under catalyst- base-free conditions. In this transformation, one intermolecular C–N bond formation is achieved at room temperature. series highly substituted 1,2,4-triazole-based 3-nitrochromanes were produced in good excellent yields, up 86%. The relative configuration the Michael adducts was confirmed by X-ray crystallographic analysis. High yield, easy accessibility a wide variety functional group tolerance are key features aza-Michael­ reaction.

Language: Английский

Citations

1
Tunable Zinc-Mediated Reductive Cyclization of Diastereomeric 3-Nitro-4-phenacyl-2-(trihalomethyl)chromanes to Fused Pyrroline N-Oxides, Pyrrolines, and Pyrrolidines DOI
Vladislav Yu. Korotaev, Igor B. Kutyashev,

Maxim S. Sannikov

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1567 - 1590

Published: Jan. 20, 2024

Reductive cyclization of trans,trans- and trans,cis-isomers the 2-CF3-substituted 3-nitro-4-phenacylchromanes with Zn-based reductive systems, depending on conditions, affords 4-CF3-substituted 1,3a,4,9b-tetrahydrochromeno[3,4-b]pyrrole 3-oxides, 1,3a,4,9b-tetrahydrochromeno[3,4-b]pyrroles, or 1,2,3,3a,4,9b-hexahydrochromeno[3,4-b]pyrroles in good yields without changing relative configuration pyran ring. A similar process involving 2-CCl3-substituted is accompanied by dehalogenation to form corresponding 4-dichloromethyl-substituted fused chromanes along 3-(2-hydroxyaryl)-2-(2,2-dichlorovinyl)-5-phenyl-2H-pyrroline 1-oxides as ring opening products. The structure obtained products was reliably confirmed X-ray diffraction analysis 2D NMR spectroscopy.

Language: Английский

Citations

0