Tag: M.W=150-200

Liu, Hailong published the artcileThree-Step One-Pot Synthesis of 1,4-Dihydropyrazolo[4,3-b|indoles Using Copper Catalysis, SDS of cas: 220943-23-7, the publication is European Journal of Organic Chemistry (2014), 2014(5), 1047-1052, database is CAplus.

A convenient three-step one-pot copper-catalyzed method has been developed for the preparation of pyrazolo[4,3-b]indoles, new indole-based compounds with potential biol. activity. Treatment of various hydrazines, including alkyl hydrazines, with indole-2-carbaldehydes generated the corresponding products in moderate to good yields without protection of the indole N-1 moiety. In addition, LiOH was used as a base in the copper-catalyzed coupling reaction. Microwave heating was used to accelerate the iodination of indoles and the C-N bond formation.

European Journal of Organic Chemistry published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C9H6FNO, SDS of cas: 220943-23-7.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Tian, Fei published the artcileCatalytic asymmetric dipolar cycloadditions of indolyl delocalized metal-allyl species for the enantioselective synthesis of cyclopenta [b]indoles and pyrrolo[1,2-a]indoles, Application of 5-Fluoro-1H-indole-2-carbaldehyde, the publication is Science China: Chemistry (2021), 64(1), 34-40, database is CAplus.

Herein, a novel indolyl substituted metal-allyl zwitterionic intermediates through the decarboxylation of conveniently available vinyl indoloxazolidones, which could be regarded as two types of dipolar species through the anionic delocalization was disclosed. The palladium-π-allyl species tended to served as an all-carbon 1,3-dipole in the asym. [3+2] cycloaddition with electron-deficient alkenes, which furnished polysubstituted cyclopenta[b]indoles I [R¹ = H, 7-F, 7-Cl, etc.; R² = Ph, 1-naphthyl, 2-furanyl, etc.; R³ = CN, CO₂Me] with high regio- and stereoselectivities. Meanwhile, the iridium-π-allyl species was recognized as an aza-1,3-dipole in asym. [3+2] cycloaddition with in situ generated C1 ammonium enolates, afforded pyrrolo[1,2-a]indoles II [R¹ = H, 7-F, 7-Cl, etc.; R⁴ = CH:CHCH₃, Ph, 3-thienyl, etc.] with high diastereo- and enantioselectivities. In addition, the dipolar cycloadditions could be easily scaled-up and several synthetic transformations of the cycloadducts were demonstrated for the rapid synthesis of diverse chiral polycyclic indoles.

Science China: Chemistry published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C9H8BrF3, Application of 5-Fluoro-1H-indole-2-carbaldehyde.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zhang, Jitan published the artcilePd(II)-Catalyzed enantioconvergent twofold C-H annulation to access atropisomeric aldehydes: a platform for diversity-oriented-synthesis, Computed Properties of 220943-23-7, the publication is Organic Chemistry Frontiers (2021), 8(13), 3404-3412, database is CAplus.

Herein, the first Pd(II)-catalyzed atroposelective dual C-H annulative strategy for the assembly of axially chiral aldehyde frameworks such as I [R = Me, Et, i-Pr] using com. available amino acid as the transient auxiliary and chiral pool was presented. This reaction accommodated a broad substrate scope to give atropisomeric aldehydes bearing both C-C and N-C chiral axes in good yields (up to 95%) with excellent enantioinduction (up to 99%). The utility of this synthetic methodol. was testified by various practical late-stage transformations, thereby accomplishing diversity-oriented synthesis of structurally diverse biaryl atropisomers and several functionalized axially chiral species such as bifunctional organocatalysts. Moreover, a series of mechanistic studies had provided more details for this catalytic transformation.

Organic Chemistry Frontiers published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C20H17FO4S, Computed Properties of 220943-23-7.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Gao, Yuning published the artcileEnantioselective Synthesis of Polycyclic Indole Derivatives Based on aza-Morita-Baylis-Hillman Reaction, HPLC of Formula: 220943-23-7, the publication is ACS Catalysis (2015), 5(11), 6608-6614, database is CAplus.

A chiral phosphine-catalyzed asym. aza-Morita-Baylis-Hillman reaction between indole-derived sulfonyl imines and bis(3-chlorophenyl)methyl acrylate has been developed, giving the desired adducts in good yields and enantiomeric excess values along with the further transformations to polycyclic indoles such as dihydropyrido[1,2-a]indole and dihydropyrazino[1,2-a]indole skeleton.

ACS Catalysis published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C9H6FNO, HPLC of Formula: 220943-23-7.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Outlaw, Victor K. published the artcileUnusual blue-shifted acid-responsive photoluminescence behavior in 6-amino-8-cyanobenzo[1,2-b]indolizines, Recommanded Product: 5-Fluoro-1H-indole-2-carbaldehyde, the publication is RSC Advances (2016), 6(66), 61249-61253, database is CAplus and MEDLINE.

6-Amino-8-cyanobenzo[1,2-b]indolizines, a new class of photoluminescent materials, exhibit reversible pH-dependent optical properties characterized by an uncommon and dramatic blue shift in fluorescence emission when protonated. Acid titration and NMR spectroscopy experiments reveal that, rather than the anticipated N-protonation, C-protonation and loss of aromaticity is responsible for the observed photophys. changes. Efficient synthesis from indole-2-carboxaldehydes makes variously substituted versions of this nucleus readily available to tune optical and pH effects.

RSC Advances published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C9H6FNO, Recommanded Product: 5-Fluoro-1H-indole-2-carbaldehyde.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zhang, Yan-Yan published the artcileDual-role of PtCl₂ catalysis in the intramolecular cyclization of (hetero)aryl-allenes for the facile construction of substituted 2,3-dihydropyrroles and polyheterocyclic skeletons, Safety of 5-Fluoro-1H-indole-2-carbaldehyde, the publication is Chemical Communications (Cambridge, United Kingdom) (2017), 53(44), 5966-5969, database is CAplus and MEDLINE.

A Pt(II)-catalyzed cyclization of (hetero)aryl-allenes were developed, providing controllable synthesis of substituted 2,3-dihydropyrroles and polyheterocyclic skeletons. Another notable feature of this method was the dual-role of the Pt(II) catalyst: initiation of the migration of the (hetero)arylmethylene group and the subsequent Friedel-Crafts type annulation.

Chemical Communications (Cambridge, United Kingdom) published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C5H5F3O2, Safety of 5-Fluoro-1H-indole-2-carbaldehyde.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Lillich, Felix F. published the artcileStructure-Based Design of Dual Partial Peroxisome Proliferator-Activated Receptor γ Agonists/Soluble Epoxide Hydrolase Inhibitors, COA of Formula: C11H11NO2, the publication is Journal of Medicinal Chemistry (2021), 64(23), 17259-17276, database is CAplus and MEDLINE.

A dual partial PPARγ agonist/sEH inhibitor using a structure-guided approach was designed. Exhaustive structure-activity relationship studies lead to the successful optimization of the designed lead. Crystal structures of one representative compound with both targets revealed potential points for optimization. The optimized compounds exhibited favorable metabolic stability, toxicity, selectivity, and desirable activity in adipocytes and macrophages.

Journal of Medicinal Chemistry published new progress about 57663-18-0. 57663-18-0 belongs to indole-building-block, auxiliary class Indole,Ester, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, COA of Formula: C11H11NO2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Lorton, Charlotte published the artcilePhosphine-Promoted Synthesis of 9H-Pyrrolo[1,2-a]indole Derivatives via an γ-Umpolung Addition/Intramolecular Wittig Reaction, Quality Control of 220943-23-7, the publication is Journal of Organic Chemistry (2018), 83(10), 5801-5806, database is CAplus and MEDLINE.

The synthesis of substituted 9H-pyrrolo[1,2-a]indole products from 1H-indole-2-carbaldehydes and allenoates is described, using a phosphine-promoted Michael addition/intramol. Wittig reaction. This halide- and base-free methodol. provides an efficient access to different tricyclic nitrogen-containing heterocycles (18 examples, 32-88% isolated yields).

Journal of Organic Chemistry published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C9H6FNO, Quality Control of 220943-23-7.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Saleh, Nidal published the artcileSynthesis of 9H-Pyrrolo[1,2-a]indole and 3H-Pyrrolizine Derivatives via a Phosphine-Catalyzed Umpolung Addition/Intramolecular Wittig Reaction, Formula: C9H6FNO, the publication is Journal of Organic Chemistry (2016), 81(10), 4371-4377, database is CAplus and MEDLINE.

The first umpolung addition/intramol. Wittig reaction, catalytic in phosphine, is described. The in situ phosphine oxide reduction was accomplished by the use of silane and a catalytic amount of bis(4-nitrophenyl)phosphate. This catalytic protocol is applicable to the synthesis of a wide range of functionalized 9H-pyrrolo[1,2-a]indoles and pyrrolizines (18 examples, 70-98% yields).

Journal of Organic Chemistry published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C9H6FNO, Formula: C9H6FNO.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Ghosh, Avipsa published the artcileCoupling Catalytic Alkene Hydroacylation and α-Arylation: Enantioselective Synthesis of Heterocyclic Ketones with α-Chiral Quaternary Stereocenters, Safety of 5-Fluoro-1H-indole-2-carbaldehyde, the publication is ACS Catalysis (2016), 6(4), 2673-2680, database is CAplus.

We report a strategy that combines alkene hydroacylation and enantioselective α-(hetero)arylation reactions to form a wide variety of nitrogen-containing heterocyclic ketones bearing α-chiral quaternary stereogenic centers. Exo-selective, intramol. Ni-catalyzed hydroacylations of N-homoallylindole- and N-homoallylpyrrole-2-carboxaldehydes form α-substituted six-membered heterocyclic ketones in up to 95% yield, while N-heterocyclic carbene (NHC) catalyzed hydroacylations of N-allylindole- and N-allylpyrrole-2-carboxaldehydes form α-substituted five-membered heterocyclic ketones in up to 99% yield. The racemic five- and six-membered products of Ni- and NHC-catalyzed hydroacylation reactions are readily transformed into heterocyclic ketones containing an α-chiral quaternary stereogenic center by enantioselective Ni-catalyzed α-arylation and α-heteroarylation reactions. The chiral, nonracemic products formed through a combination of alkene hydroacylation and α-(hetero)arylation reactions are formed in moderate to high yields (44-99%) with excellent enantioselectivities (typically >95% ee). The identity of the precatalyst for Ni-catalyzed α-(hetero)arylation is dictated by the identity of the α-substituted heterocyclic ketone starting material. α-(Hetero)arylations of six-membered heterocyclic ketones occur at 65-85 °C in the presence of a catalyst generated in situ from Ni(COD)₂ and (R)-BINAP or (R)-DIFLUORPHOS. α-(Hetero)arylation of five-membered heterocyclic ketones must be conducted at room temperature in the presence of an [((R)-BINAP)Ni(η²-NC-Ph)] precatalyst or a catalyst generated in situ from Ni(COD)₂, (R)-DIFLUORPHOS, and benzonitrile.

ACS Catalysis published new progress about 220943-23-7. 220943-23-7 belongs to indole-building-block, auxiliary class Indole,Fluoride,Aldehyde, name is 5-Fluoro-1H-indole-2-carbaldehyde, and the molecular formula is C9H6FNO, Safety of 5-Fluoro-1H-indole-2-carbaldehyde.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles