4.8 Article

I2/FeCl3-Catalyzed Domino Reaction of Aurones with Enamino Esters for the Synthesis of Highly Functionalized Pyrroles

Related references

Note: Only part of the references are listed.
Article Chemistry, Applied

Iodine-Catalyzed Double [4+2] Oxidative Annulations for the Synthesis of Bipyrazines from Ketones and Diamines by a Domino Strategy

Yuxin Ding et al.

Summary: An iodine-catalyzed double [4+2] oxidative annulation of ketones and diamines is reported, leading to the synthesis of substituted dimeric pyrazines under metal-free conditions through a multi-pathway coupled domino strategy. During this process, one C-C and four C-N bonds are formed from two ketones and two diamines.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Article Chemistry, Organic

Synthesis of Substituted Thiophenes through Dehydration and Heterocyclization of Alkynols

Jian Li et al.

Summary: A method for obtaining substituted thiophenes with functional potential through metal-free dehydration and sulfur cyclization was described. The reaction of alkynols with elemental sulfur (S-8) or EtOCS2K yielded moderate-to-good yields. The method showcased the base-free generation of a trisulfur radical anion (S-3(center dot-)) and its addition to alkynes as an initiator. This research broadens the applications of S-3(center dot-) in the synthesis of sulfur-containing heterocycles.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Review Chemistry, Organic

Recent developments in the synthesis of nitrogen-containing heterocycles from β-aminovinyl esters/ketones as C=C-N donors

Xiao-Feng Xia et al.

Summary: This review summarized a series of synthetic methods using beta-aminovinyl esters (ketones) to synthesize bioactive heterocyclic frameworks, providing new opportunities and expanding the toolbox of synthetic chemistry reactions.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Organic

Gold-Catalyzed Cyclization of Ynones Involving cis-Hydrofunctionalizations: Rapid Assembly of C-, O-, or S-Functionalized Pyrroles by a Single Methodology

Miaomiao Pei et al.

Summary: This study reports a gold-catalyzed cyclization reaction for the synthesis of functionalized pyrroles with wide versatility and high reaction applicability. Moreover, cis-hydrofunctionalizations of ynones are involved in these reactions.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

I2-Mediated [3+2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides: selective synthesis of iodine-functionalized and non-iodine-functionalized fused imidazoles

Yong-Ji Hu et al.

Summary: In this study, an I-2-mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides was demonstrated. This method allows for the selective synthesis of iodine-functionalized and non-iodine-functionalized fused imidazoles, with the potential for further chemical modifications of the iodine-functionalized products.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Organic

Visible-Light-Mediated Synthesis of Thio-Functionalized Pyrroles

Ashish Kumar Sahoo et al.

Summary: An effective method for the green-light-induced synthesis of thio-functionalized pyrroles has been established, using beta-ketodinitriles and thiophenols as reactants and eosin Y as the photocatalyst. The study also demonstrates the scalability of the synthesis and introduces some useful synthetic modifications for the thio-functionalized pyrroles.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Solvent-Free Mechanosynthesis of Polysubstituted 1,2-Dihydroquinolines from Anilines and Alkyne Esters

Hui Xu et al.

Summary: We have developed a novel solvent-free ball-milling reaction method for the synthesis of polysubstituted 1,2-dihydroquinolines in moderate to excellent yields. This method features mild reaction conditions, short reaction time, and is applicable for large-scale synthesis, providing a facile and practical alternative for the synthesis of 1,2-dihydroquinoline compounds.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Organic

One-Pot Synthesis of 2-Acety1-1H-pyrroles from N-Propargylic β-Enaminones via Intermediacy of 1,4-Oxazepines

Nilay Kanova et al.

Summary: A one pot two step protocol has been developed for the synthesis of 2-acetyl-1H-pyrroles from N-propargylic beta-enaminones. The method is general, providing a diverse range of products with good to high yields and tolerating various functional groups. This operationally easy method offers a rapid access to functionalized 2-acetyl-1H-pyrroles with potential pharmacological interest.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Merging Annulation with Ring Deconstruction: Synthesis of (E)-3-(2-Acyl-1H-benzo[d]imidazol-4-yl)acrylaldehyde Derivatives via I2/FeCl3-Promoted Dual C(sp3)-H Amination/C-N Bond Cleavage

Cheng Xu et al.

Summary: A novel I-2/FeCl3-promoted cascade reaction was developed for the convenient synthesis of (E)-3-(2-acyl-1H-benzo[d]imidazol-4-yl)acrylaldehydes by merging annulation with ring deconstruction, unlocking the new reactivity of 8-aminoquinolines and providing a platform for the ring opening of unactivated N-heteroaromatic compounds. Preliminary mechanistic investigation suggested that dual C(sp(3))-H amination/C-N bond cleavage were key reaction steps, and late-stage modification successfully delivered pyrazole and isoxazole derivatives, increasing the practicability and application potential of this methodology in organic synthesis.

ORGANIC LETTERS (2021)

Review Chemistry, Organic

Recent Advancements in Pyrrole Synthesis

Satish Chandra Philkhana et al.

Summary: This review article highlights selected examples of functionalized pyrrole synthesis from 2014 to 2019, organized by starting materials and discussing plausible reaction mechanisms.

SYNTHESIS-STUTTGART (2021)

Article Chemistry, Multidisciplinary

Synthesis of Pyrroles via Consecutive 6π-Electrocyclization/Ring-Contraction of Sulfilimines

Franz-Lucas Haut et al.

Summary: This study presents a new synthetic approach to polysubstituted pyrroles using 2,5-dihydrothiophenes, with the ring-opening of the heterocycle providing access to a panel of 1,3-dienes that undergo pyrrole formation in the presence of inexpensive chloramine-T trihydrate. The reaction is conducted in an open flask at ambient temperatures and key intermediates can be isolated by carefully adjusting the electronics and sterics of the 1,3-diene precursor. DFT studies identified a reaction mechanism involving a 6 pi-electrocyclization of a sulfilimine intermediate followed by spontaneous ring-contraction to reveal the pyrrole skeleton.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Direct C-C Bond Cleavage of 1,3-Dicarbonyl Compounds as a Single-Carbon Synthon: Synthesis of 2-Aryl-4-quinolinecarboxylates

You Zhou et al.

Summary: A novel [2+1+3] cyclization reaction has been established for the synthesis of 2-aryl-4-quinolinecarboxylates from aryl methyl ketones, arylamines, and 1,3-dicarbonyl compounds. This metal-free process achieves C-C bond cleavage of 1,3-dicarbonyl compounds as a single-carbon synthon, showing high efficiency, good substrate compatibility, and practicality in the synthesis of bioactive molecules.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Annulation of CF3-Imidoyl Sulfoxonium Ylides with 1,3-Dicarbonyl Compounds: Access to 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles

Si Wen et al.

Summary: A lithium-bromide-promoted nucleophilic substitution/annulation cascade reaction has been developed for the synthesis of 1,2,3-trisubstituted 5-trifluoromethylpyrroles from CF3-imidoyl sulfoxonium ylides and 1,3-dicarbonyl compounds, yielding products in 27-78% yield. The reaction exhibits a broad substrate scope and produces dimethyl sulfoxide and water as byproducts.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Silver-Catalyzed Regioselective Synthesis of Highly Substituted 2-Trifluoromethyl Pyrroles

Wei Wu et al.

Summary: A highly efficient and regioselective synthesis of highly substituted 2-trifluoromethyl pyrrole derivatives is reported via a silver-catalyzed cyclization of vinyl azides with ethyl 4,4,4-trifluoro-3-oxobutanoate. Various types of alpha-(heteo)aryl, alkyl, alpha-aryl, and alpha,beta-disubstituted vinyl azides can participate in this transformation. The proposed reaction mechanism involves the addition of in situ generated 2H-azirine to the diketone species, followed by intramolecular addition, N-C-1 cleavage, and elimination.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Regiodivergent Synthesis of 4,5′- and 4,4′-Imidazolinyl Spiropyrazolones from 4-Alkylidene Pyrazolones and Amidines

Hui Xu et al.

Summary: By utilizing different catalysts under different conditions, it is possible to selectively synthesize structurally diverse 4,5'- and 4,4'-imidazolinyl spiropyrazolones, leading to the development of a powerful metal-free method.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

I2-Catalyzed oxidative dehydrogenative tandem cyclization of 2-methylquinolines, arylamines and 1,4-dioxane

Hongrui Qi et al.

Summary: In this novel I-2-catalyst oxidative dehydrogenative tandem cyclization reaction, 2-methylquinolines, arylamines, and 1,4-dioxane were used as substrates to construct 2-([2,2'-biquinolin]-3-yloxy)ethan-1-ol derivatives under metal-free conditions. This transformation involved the cleavage of 7 C-H bonds, 2 N-H bonds, and 1 C-O bond, leading to the formation of 2 C-C bonds, 1 C-N bond, and 1 O-H bond, with the opening of the 1,4-dioxane ring and the formation of a 2-(vinyloxy)ethan-1-ol group in the process.

ORGANIC CHEMISTRY FRONTIERS (2021)

Review Chemistry, Organic

Recent Advances in the Synthesis of Pyrroles

Sarosh Iqbal et al.

CURRENT ORGANIC CHEMISTRY (2020)

Review Chemistry, Multidisciplinary

Transition Metal-Catalyzed Tandem Reactions of Ynamides for Divergent N-Heterocycle Synthesis

Feng-Lin Hong et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

Review Chemistry, Organic

Developments towards synthesis of N-heterocycles from amidines via C-N/C-C bond formation

Wei Guo et al.

ORGANIC CHEMISTRY FRONTIERS (2019)

Article Chemistry, Organic

Reaction Mechanism of Iodine-Catalyzed Michael Additions

Daniel von der Heiden et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

α-Diazo oxime ethers for N-heterocycle synthesis

Subin Choi et al.

CHEMICAL COMMUNICATIONS (2017)

Review Chemistry, Medicinal

Pyrrole: An emerging scaffold for construction of valuable therapeutic agents

Somnath S. Gholap

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2016)

Review Chemistry, Organic

Iodine-mediated synthesis of heterocycles via electrophilic cyclization of alkynes

Trapti Aggarwal et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

Review Chemistry, Multidisciplinary

α,β-Unsaturated Diazoketones as Useful Platforms in the Synthesis of Nitrogen Heterocycles

Antonio C. B. Burtoloso et al.

ACCOUNTS OF CHEMICAL RESEARCH (2015)

Review Chemistry, Multidisciplinary

Titanium-Catalyzed Multicomponent Couplings: Efficient One-Pot Syntheses of Nitrogen Heterocycles

Aaron L. Odom et al.

ACCOUNTS OF CHEMICAL RESEARCH (2015)

Article Chemistry, Multidisciplinary

Construction of N-containing heterocycles via oxidative intramolecular N-H/X-H coupling

Jiwen Yuan et al.

CHEMICAL COMMUNICATIONS (2015)

Review Chemistry, Multidisciplinary

Recent advances in the synthesis of pyrroles by multicomponent reactions

Veronica Estevez et al.

CHEMICAL SOCIETY REVIEWS (2014)

Review Chemistry, Multidisciplinary

Recent Developments in the Synthesis of Five- and Six-Membered Heterocycles Using Molecular Iodine

Prakash T. Parvatkar et al.

CHEMISTRY-A EUROPEAN JOURNAL (2012)

Article Agronomy

Rational design of new agrochemical fungicides using substructural descriptors

Alejandro Speck-Planche et al.

PEST MANAGEMENT SCIENCE (2011)

Review Chemistry, Multidisciplinary

Dye-Sensitized Solar Cells

Anders Hagfeldt et al.

CHEMICAL REVIEWS (2010)

Review Biochemistry & Molecular Biology

Synthesis of natural products containing the pyrrolic ring

Ian S. Young et al.

NATURAL PRODUCT REPORTS (2010)

Article Chemistry, Applied

Iron(III) Salt-Catalyzed Nazarov Cyclization/Michael Addition of Pyrrole Derivatives

Masamune Fujiwara et al.

ADVANCED SYNTHESIS & CATALYSIS (2009)

Review Chemistry, Multidisciplinary

BODIPY dyes and their derivatives: Syntheses and spectroscopic properties

Aurore Loudet et al.

CHEMICAL REVIEWS (2007)

Review Chemistry, Organic

Synthetic use of molecular iodine for organic synthesis

Hideo Togo et al.

SYNLETT (2006)

Article Chemistry, Physical

Investigations into the metal species of the homogeneous iron(III) catalyzed Michael addition reactions

M Bauer et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2005)

Review Chemistry, Multidisciplinary

Iodine electrophiles in stereoselective reactions: recent developments and synthetic applications

AN French et al.

CHEMICAL SOCIETY REVIEWS (2004)

Article Biochemistry & Molecular Biology

Foundations for blockbuster drugs in federally sponsored research

RB Thompson

FASEB JOURNAL (2001)