Tag: M.W=150-200

Nishiyama, Takashi published the artcileConcise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells, Related Products of indole-building-block, the publication is European Journal of Medicinal Chemistry (2016), 561-577, database is CAplus and MEDLINE.

A convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O₂ atmosphere as an important step is reported. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions I (R¹ = R² = H, CH₃; R³ = H, 6-OCH₃, 5,6-(OCH₃)₂, 7-CH₃, 6-NO₂, etc.; R⁴ = H, MOM) have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.

European Journal of Medicinal 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, Related Products of indole-building-block.

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, Jian published the artcileCooperative N-heterocyclic Carbene and Iridium Catalysis Enables Stereoselective and Regiodivergent [3 + 2] and [3 + 3] Annulation Reactions, Recommanded Product: 5-Fluoro-1H-indole-2-carbaldehyde, the publication is ACS Catalysis (2021), 11(7), 3810-3821, database is CAplus.

A cooperative N-heterocyclic carbene (NHC)/iridium catalysis has been developed to achieve highly stereoselective and regiodivergent [3 + 2] and [3 + 3] annulation reactions of 2-indolyl allyl carbonates I (R = H, Me; R¹ = H, OMe, Me, F, Cl; R¹ = H, OMe, Cl) with enals R³CH=CHCHO (R¹ = Ph, hexyl, 4-chlorophenyl, furan-2-yl, etc.). The use of the NHC catalyst has introduced switchable homoenolate and enolate intermediates from the common enal precursor via a simple adjustment of reaction conditions in a predictable manner. This protocol furnishes two types of biol. important products, pyrrolo[1,2-a]indoles II and pyridine[1,2-a]indoles III, with high diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). Notably, all four stereoisomers of these products with two vicinal stereocenters could be afforded through permutations of the enantiomers of the two chiral catalysts. Mechanistic investigations and further computational d. functional theory calculations give an explanation of the origin of the regioselectivity. In addition, the NHC-enolate intermediate generated from formylcyclopropanes IV (R⁴ = Ph, tert-Bu, naphthalen-2-yl, etc.) was also compatible in this cooperative catalytic system and thus the arsenal of optically pure pyrrolo[1,2-a]indole products V was enriched.

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 C18H12FN, 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

Galvan, Alicia published the artcileExploiting the Multidentate Nature of Chiral Disulfonimides in a Multicomponent Reaction for the Asymmetric Synthesis of Pyrrolo[1,2-a]indoles: A Remarkable Case of Enantioinversion, Product Details of C9H6FNO, the publication is Angewandte Chemie, International Edition (2016), 55(10), 3428-3432, database is CAplus and MEDLINE.

A new multicomponent coupling reaction for the enantioselective synthesis of pyrrolo[1,2-a]indoles under the catalysis of a chiral disulfonimide is described. The high specificity of the reaction is a consequence of the multidentate character of the Bronsted acid catalyst. Insights from DFT calculations helped explain the unexpected high enantioselectivity observed with the simplest 3,3′-unsubstituted binaphthyl catalyst as a result of transition-state stabilization by a network of cooperative noncovalent interactions. The remarkable enantioinversion resulting from the simple introduction of substituents at 3- and 3′-positions, the first reported example of this phenomenon in the context of binaphthalene-derived Bronsted acid catalysis, was instead attributed to destabilizing steric interactions.

Angewandte Chemie, International Edition 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, Product Details of 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

Cheng, Hong-Gang published the artcileConvenient synthesis of tetrahydro-γ-carbolines and tetrahydroquinolines through a chemo- and regioselectivity switch by a Bronsted acid catalyzed, one-pot, multicomponent reaction, Application of 5-Fluoro-1H-indole-2-carbaldehyde, the publication is European Journal of Organic Chemistry (2010), 4976-4980, S4976/1-S4976/49, database is CAplus.

An efficient, one-pot, multicomponent reaction of aldehydes, p-methoxyaniline, and 2-vinylindoles was developed. This approach provides a practical approach to synthetically and biol. significant tetrahydro-γ-carboline and tetrahydroquinoline derivatives in good yields through a chemo- and regioselectivity switch, which can be tuned by simply changing the substituent on the indole component under identical reaction conditions.

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, 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

Pirovano, Valentina published the artcileGold-catalyzed synthesis of tetrahydrocarbazole derivatives through an intermolecular cycloaddition of vinyl indoles and N-allenamides, Safety of 5-Fluoro-1H-indole-2-carbaldehyde, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(34), 3594-3596, database is CAplus and MEDLINE.

A gold-catalyzed formal [4+2] cycloaddition of vinyl indoles and N-allenamides leading to tetrahydrocarbazoles is described. E.g., in presence of AuCl₃, [4+2] cycloaddition of vinyl indole (I) and N-allenamide (II) gave 83% tetrahydrocarbazole derivative (III). Moreover, new multicomponent reactions of vinyl indoles with two allene mols. are reported.

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 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

Wani, Imtiyaz Ahmad published the artcileTemperature-modulated diastereoselective transformations of 2-vinylindoles to tetrahydrocarbazoles and tetrahydrocycloheptadiindoles, HPLC of Formula: 220943-23-7, the publication is Organic & Biomolecular Chemistry (2018), 16(16), 2910-2922, database is CAplus and MEDLINE.

Direct and expedient access to densely substituted tetrahydrocarbazoles I [R¹ = H, F; R² = H, Me, CH₂CH:CH₂; R³ = OMe, OEt, Ph] and tetrahydrocycloheptadiindoles bearing multiple contiguous stereocenteres II [R¹ = H, F, Cl, Me] were achieved via a two-fold divergent diastereoselective (dr up to >99:1) transformation of 2-vinylindoles. The high-yielding conversions (yield up to 87%) that were amenable for a wide range of substituted 2-vinylindoles proceeded through Lewis acid-catalyzed [4 + 2] and [4 + 3] cyclization-aromatization cascade reactions, resp., involving a heretofore-unprecedented reversal of the polarity (umpolung) of 2-vinylindoles. The two synthetic routes were effortlessly transposable into each other by merely modulating the temperature to furnished the corresponding products in a selective and exclusive fashion. In addition, another novel synthetic route to tetrahydroindolocarbazoles was developed that advances via a formal [4+2] cyclization of 4-vinylindoles involving sequential C3 Michael addition-dearomatization-aromatization cascade reactions. Diastereo- and chemoselective preparation of tetrahydrocarbazoles and tetrahydrocycloheptadiindoles via Fe(OTf)₃ catalyzed tandem cyclization-aromatization of vinylindoles.

Organic & Biomolecular 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 C7H4ClIO2, 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