71293-59-9 | - Indole Building Blocks

Qin, Hui’s team published research in Tetrahedron in 2018-11-22 | CAS: 71293-59-9

Tetrahedron published new progress about Cyclopropanation. 71293-59-9 belongs to class indole-building-block, name is 5,6-Dichloroindolin-2-one, and the molecular formula is C8H5Cl2NO, Quality Control of 71293-59-9.

Qin, Hui published the artcileA convenient cyclopropanation process of oxindoles via bromoethylsulfonium salt, Quality Control of 71293-59-9, the main research area is oxindole bromoethylsulfonium triflate cyclopropanation; spirocyclopropane indolinone preparation.

A practical convenient conversion of oxindoles into the corresponding spirocyclopropane-oxindoles, e.g., I, is achieved efficiently using bromoethylsulfonium salt, which is easily prepared on a large scale and is stable crystalline This reaction of bromoethylsulfonium salt with different substituted unprotected oxindoles proceeded under mild condition and provided moderate yields.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zhou, Mingwei’s team published research in RSC Advances in 2017 | CAS: 71293-59-9

RSC Advances published new progress about Cyclopropanation. 71293-59-9 belongs to class indole-building-block, name is 5,6-Dichloroindolin-2-one, and the molecular formula is C8H5Cl2NO, Application of 5,6-Dichloroindolin-2-one.

Zhou, Mingwei published the artcileZinc triflate-mediated cyclopropanation of oxindoles with vinyl diphenyl sulfonium triflate: a mild reaction with broad functional group compatibility, Application of 5,6-Dichloroindolin-2-one, the main research area is spirocyclopropyloxindole preparation; oxindole vinyl diphenyl sulfonium triflate zinc triflate mediated cyclopropanation.

The first use of zinc triflate for the cyclopropanation of unprotected oxindoles with vinyl di-Ph sulfonium triflate salt to afford spiro[cyclopropane-1,3′-indoline]-2′-ones I [R = 5-OH, 6-F, 7-Cl, 4-Br, etc.] was reported. The reaction proceeded under ambient conditions and consistently provided high yields with broad functional group tolerability. The utility for the late-stage functionalization (LSF) of complex mols. was demonstrated.

Kraynack, Erica A.’s team published research in Tetrahedron Letters in 1998-10-15 | CAS: 71293-59-9

Tetrahedron Letters published new progress about Regiochemistry. 71293-59-9 belongs to class indole-building-block, name is 5,6-Dichloroindolin-2-one, and the molecular formula is C8H5Cl2NO, Related Products of indole-building-block.

Kraynack, Erica A. published the artcileAn improved procedure for the regiospecific synthesis of electron deficient 4- and 6-substituted isatins, Related Products of indole-building-block, the main research area is isatin electron deficient regiospecific preparation; nitrochlorobenzene substitution malonate; chloroisatin regiospecific preparation; benzoylisatin regiospecific preparation.

The regiospecific synthesis of C-4 and C-6 substituted isatins I (R = H, Cl; R1 = H, Cl; R2 = H, Cl, Bz, 4-MeC6H4CO, 4-ClC6H4CO, 4-MeOC6H4CO) in four steps from halonitrobenzenes II (X = Cl, F) was investigated for a variety of substrates. The procedure makes use of readily available, easily handled materials and in most cases purification of neither intermediates nor final products is required. Yields of isatins I are between 26 and 75%. Improved yields of known isatins are reported as well as the syntheses of previously unreported isatins. This method, taken together with known procedures, provides for the synthesis of the full complement of isatin regioisomers.

Chen, Jiong J.’s team published research in Journal of Medicinal Chemistry in 2000-06-15 | CAS: 71293-59-9

Journal of Medicinal Chemistry published new progress about Antiviral agents. 71293-59-9 belongs to class indole-building-block, name is 5,6-Dichloroindolin-2-one, and the molecular formula is C8H5Cl2NO, Related Products of indole-building-block.

Chen, Jiong J. published the artcileSynthesis and Antiviral Evaluation of Trisubstituted Indole N-Nucleosides as Analogues of 2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB), Related Products of indole-building-block, the main research area is ribofuranosyl chloroindole analog stereochem preparation antiviral cytomegalovirus inhibition; indole nucleoside preparation cytotoxicity virucide structure activity.

2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB) and 2-bromo-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (BDCRB) are nucleosides that exhibit strong and selective activity against human cytomegalovirus (HCMV). Selected polyhalogenated indole nucleosides have now been synthesized as 3-deaza analogs of the benzimidazole nucleosides using the sodium salt glycosylation method. 2-Benzylthio-1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5,6-dichloroindole was prepared stereoselectively via the coupling of a 2-deoxyribofuranosyl α-chloride derivative with the sodium salt of 2-benzylthio-5,6-dichloroindole. This compound was then elaborated into the targeted 2-benzylthio-1-(β-D-ribofuranosyl)-5,6-dichloroindole in five steps. 2,5,6-Trichloro-(1-β-D-ribofuranosyl)indole was prepared using the same synthetic route with 2,5,6-trichloroindole as the starting material. The authors were subsequently able to prepare 2,5,6-trichloro-1-(β-D-ribofuranosyl)indole in three steps using a modification of the sodium salt glycosylation method. 2-Bromo-5,6-dichloro-1-(β-D-ribofuranosyl)indole was also prepared using the same procedures. Target compounds were tested for activity against HCMV, herpes simplex virus type 1 (HSV-1), and human herpes virus six (HHV-6) and for cytotoxicity. All of the compounds were less active against HCMV than TCRB and weakly active or inactive against HSV-1 and HHV-6.

Qin, Hui’s team published research in Journal of Organic Chemistry in 2019-11-01 | CAS: 71293-59-9

Journal of Organic Chemistry published new progress about Cross-coupling reaction. 71293-59-9 belongs to class indole-building-block, name is 5,6-Dichloroindolin-2-one, and the molecular formula is C8H5Cl2NO, Computed Properties of 71293-59-9.

Qin, Hui published the artcileA Mild and Direct C(sp3)-S Cross-Coupling of Oxindoles with Thiols: Synthesis of Unsymmetrical 3-Thiooxindoles, Computed Properties of 71293-59-9, the main research area is thiooxindole preparation coupling oxindole thiol.

Herein, an operationally simple and mild strategy to construct sulfenation of oxindoles with a series of thiols in the absence of transition metals was developed. This methodol. provides an efficient way to directly form a C-S bond at the C-3 position of oxindoles under mild reaction conditions with a cheap and common solvent and base in moderate to good yields.