Month: February 2023

Lewis acid-mediated synthesis of mono- and tris-indole adducts from chiral aziridines was written by Macha, Lingamurthy;Singh, Deepak;Rhee, Hyong-Jin;Ha, Hyun-Joon. And the article was included in Organic & Biomolecular Chemistry in 2020.Synthetic Route of C8H6FN This article mentions the following:

Lewis acid-mediated regio- and stereoselective nucleophilic addition of 2- or 3-substituted indoles to non-activated aziridine-2-carboxaldehydes in dioxane afforded 2-(indol-3-ylhydroxymethyl)aziridines such as I [R = cyclohexyl, Bn, CH(Me)Ph; R¹ = H, 5-F, 5-Br, etc.; R² = 2-CO₂Me, CO₂Et] whose ring opening with various nucleophiles rendered multi-substituted tryptamine derivatives, e.g., II. The reaction of the same aziridine-2-carboxaldehyde with three moles of indole in dichloromethane yielded tris-indole adducts, e.g., III 尾-(3,3′-bisindolyl)methyl (BIM) tryptamines from sequential steps including nucleophilic addition to aldehyde, Michael type Friedel-Crafts alkylation of the mono-adduct followed by regio- and stereoselective ring-opening of the aziridine ring. In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Synthetic Route of C8H6FN).

7-Fluoroindole (cas: 387-44-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Synthetic Route of C8H6FN

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

Palladium-Catalyzed Asymmetric Dearomative Carbonylation of Indoles was written by Li, Qiuyu;Zhang, Yunchu;Zeng, Yuye;Fan, Yujing;Lin, Aijun;Yao, Hequan. And the article was included in Organic Letters in 2022.COA of Formula: C14H10ClN This article mentions the following:

Herein, authors disclose a strategy for the asym. dearomatization of N-arylacyl indoles via a palladium-catalyzed tandem Heck/carbonylation, leading to an array of indoline-3-carboxylates bearing vicinal C2-aza-quaternary and C3 tertiary stereocenters in high yields and excellent enantio- and diastereoselectivities. This study is an important advance in the field of asym. carbonylation and enantioselective dearomatization reactions. In the experiment, the researchers used many compounds, for example, 5-Chloro-2-phenyl-1H-indole (cas: 23746-76-1COA of Formula: C14H10ClN).

5-Chloro-2-phenyl-1H-indole (cas: 23746-76-1) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.COA of Formula: C14H10ClN

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

Synthetic studies toward welwitindolinone alkaloids. Tandem aldol-michael reaction to form the carbocyclic core of welwitindolinones was written by Shima, Masato;Toyota, Masahiro. And the article was included in Heterocycles in 2015.Synthetic Route of C9H8BrN This article mentions the following:

A tandem aldol-Michael reaction of silyl enol ether of indolylcyclohexanone with acetone to effectively construct a bridged ketone, which is the carbocyclic core of the welwitindolinone family. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methyl-1H-indole (cas: 590417-55-3Synthetic Route of C9H8BrN).

4-Bromo-1-methyl-1H-indole (cas: 590417-55-3) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Synthetic Route of C9H8BrN

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

An Unprecedented Pseudo-[3+2] Annulation between N-(4-Methoxyphenyl)aldimines and Aqueous Glutaraldehyde: Direct Synthesis of Pyrrole-2,4-dialdehydes was written by Ramaraju, Panduga;Mir, Nisar A.;Singh, Deepika;Sharma, Preetika;Kant, Rajni;Kumar, Indresh. And the article was included in European Journal of Organic Chemistry in 2017.Electric Literature of C8H6FNO This article mentions the following:

A new method for the direct one-pot synthesis of substituted pyrrole-2,4-dialdehdyes was developed. This overall pseudo-[3+2]-annulation reaction between glutaraldehyde and N-(4-methoxyphenyl)aldimines proceeds through proline-catalyzed direct Mannich reaction/cyclization, followed by 2-iodoxybenzoic acid mediated oxidative rearrangement of the in situ generated intermediate to give pyrrole-2,4-dialdehydes in high yields (up to 80 %). In the experiment, the researchers used many compounds, for example, 5-Fluoroindolin-2-one (cas: 56341-41-4Electric Literature of C8H6FNO).

5-Fluoroindolin-2-one (cas: 56341-41-4) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Electric Literature of C8H6FNO

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

Facile One-Pot Access to 伪-Diazo-尾-ketosulfones from Sulfonyl Chlorides and 伪-Haloketones was written by Dar’in, Dmitry;Kantin, Grigory;Bakulina, Olga;Krasavin, Mikhail. And the article was included in Synthesis in 2020.COA of Formula: C10H8ClNO3S This article mentions the following:

A convenient one-pot approach to the preparation of 伪-diazo-尾-ketosulfones R¹SO₂C(=N₂)C(O)R² [R¹ = Me, cyclohexyl, Ph, etc.; R² = Me, Ph, 4-FC₆H₄, etc.] from sulfonyl chlorides was described. It involved the conversion of sulfonyl chloride to sodium sulfinate, alkylation of latter with 伪-haloketones followed by diazo transfer using ‘sulfonyl-azide-free’ (SAFE) protocol in aqueous medium. The simple and expedient method relied on readily available starting materials and provided facile access to a wide variety of valuable diazo reagents for organic synthesis. In the experiment, the researchers used many compounds, for example, 1-Acetylindoline-5-sulfonyl chloride (cas: 52206-05-0COA of Formula: C10H8ClNO3S).

1-Acetylindoline-5-sulfonyl chloride (cas: 52206-05-0) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.COA of Formula: C10H8ClNO3S

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

Dearomative spirocyclization via visible-light-induced reductive hydroarylation of non-activated arenes was written by Chi, Zhuomin;Gao, Yuzhen;Yang, Lei;Zhou, Chunlin;Zhang, Meng;Cheng, Peiming;Li, Gang. And the article was included in Chinese Chemical Letters in 2022.Safety of 5-Bromo-2-phenyl-1H-indole This article mentions the following:

A visible-light-induced spirocyclizative hydroarylation via reductive dearomatization of a series of non-activated arenes including 2-Ph indoles and naphthalene derivatives under mild conditions was described. An intriguing chemoselective dearomative hydroarylation of 2-Ph indoles was presented. This dearomative hydroarylation protocol rapidly delivered valuable spirocycles with carbon-carbon double bonds from readily accessible aromatic precursors in a single step. In the experiment, the researchers used many compounds, for example, 5-Bromo-2-phenyl-1H-indole (cas: 83515-06-4Safety of 5-Bromo-2-phenyl-1H-indole).

5-Bromo-2-phenyl-1H-indole (cas: 83515-06-4) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Safety of 5-Bromo-2-phenyl-1H-indole

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

Some reactions of 4,7,8,9-tetrahydroisoindoline and perhydroisoindole was written by Rice, Leonard M.;Grogan, Charles H.. And the article was included in Journal of Organic Chemistry in 1955.Quality Control of Octahydro-1H-isoindole This article mentions the following:

Reduction of 150 g. cis-螖⁴-tetrahydrophthalimide with 60 g. LiAlH₄ in 1.7 l. Et₂O 24 hrs. by the Soxhlet apparatus method and decomposition of the excess LiAlH₄ with H₂O gives 60 g. 4,7,8,9-tetrahydroisoindoline (I), b₁₅ 76-80掳, b₂₆ 90-3掳 (phenylthiourea derivative, m. 164-5掳; “naphthylurea derivative,” m. 216-17掳; phenylurea derivative, m. 152.5-3.5掳; p-bromophenylsulfonamide derivative, m. 102-3掳; HCl salt, m. 131.5-2.5掳). Hydrogenation of 32 g. I in 300 cc. MeOH with 0.5 g. PtO₂ at 20掳 gives perhydroisoindole (HCl salt, m. 123.5-5掳; picrate, m. 162-3掳; phenylurea derivative, m. 133-5掳; phenylthiourea derivative, m. 176-8掳; naphthylurea derivative, m. 182-3.5掳). Refluxing 17.7 g. I and 5.4 g. CH₂ClCN 4 hrs. in 100 cc. PhMe gives 69% N-(cyanomethyl)-I (II), b_0.4 80掳, b_0.2 67掳, n_D²⁰ 1.5031. Adding dropwise 6 g. II in 100 cc. Et₂O to 2 g. LiAlH₄ in 400 cc. Et₂O, refluxing the mixture 2 hrs., adding H₂O, and distilling the residue of the Et₂O solution give 6.1 g. N-(尾-aminoethyl)-I, b_3.5 97-101掳, n_D²⁰ 1.5067 (di-HCl salt, rectangular plates, m. 180-80.5掳). Subjecting 0.1 molar amounts of I and PhCOMe to the Mannich reaction according to Blicke (C.A. 36, 5766.6) gives 60% Ph 尾-(4,7,8,9-tetrahydro-2-isoindolinyl)ethyl ketone-HCl, m. 153-5掳. Passing 8.4-8.8 g. ethylene oxide into 25.5 g. I in 500 cc. MeOH at 0掳 and keeping the mixture overnight at 20掳 give 63% N-(尾-hydroxyethyl)-I (III), b₁ 85-90掳. Hydrogenation of 7 g. III in 100 cc. MeOH 1 hr. with 5% Pd-C gives 5.5 g. N-(尾-hydroxyethyl)perhydroisoindole (IV), b_0.75 78-82掳 [p-nitrobenzoate-HCl (V), 100%, m. 171.5-2.5掳]. Refluxing 5.01 g. III in 45 cc. C₆H₆ 2 hrs. with 5.57 g. p-O₂NC₆H₄COCl in 45 cc. C₆H₆ gives almost 100% 尾-(4,7,8,9-tetrahydroisoindolinyl)ethyl p-nitrobenzoate-HCl (VI), m. 157-8掳. Reduction of 5 g. VI in 400 cc. MeOH over 5% Pd-C at 20掳 gives 尾-(perhydroisoindolyl)ethyl p-aminobenzoate-HCl, m. 229-31掳 which is also obtained on reduction of V. Refluxing 32.03 g. I in 150 cc. PhMe 4 hrs. with 15.9 g. CH₂ClCO₂Et, filtering off the I.HCl formed, and distilling the residue of the evaporated filtrate give 21 g. Et (4,7,8,9-tetrahydroisoindolinyl)acetate (VII), b_0.2 73-5掳. Treating 10.15 g. VII in 40 cc. absolute EtOH 3 days with the calculated amount of _0.5N alc. KOH, adding the calculated amount of HCl, and evaporating the filtered solution give 4,7,8,9-tetrahydroisoindolinylacetic acid, crystallizing with 1 H₂O, m. 146-7掳. Refluxing 10.5 g. VII in 50 cc. 95-100% (CH₂NH₂)₂ 8 hrs. and fractionally distilling the mixture give N-(₂-imidazolemethyl)-4,7,8,9-tetrahydroisoindoline, b_0.5 173-9掳, which, with alc. HCl, gives the di-HCl salt-H₂O, m. 176.5-8.5掳. Treating 8.5 g. IV in 50 cc. C₆H₆ overnight with 11.5 g. Ph₂CHCOCl, refluxing the mixture 2 hrs., extracting the cooled C₆H₆ solution with 10% HCl, making the acid solution alk., extracting with Et₂O, and treating the residue of the Et₂O extract in EtOH with alc. HCl give 尾-(perhydroisoindolyl)ethyl diphenylacetate-HCl, m. 129-30掳. Adding dropwise 26.55 g. acrylonitrile in C₆H₆ to 50.08 g. N-methylpiperazine in 150 cc. C₆H₆, refluxing the mixture several hrs., and keeping it overnight gives 79.5% N-methyl-N’-(cyanoethyl)piperazine, b_0.3 68-72掳, n_D²⁰ 1.4744, which (58 g.), reduced with LiAlH₄, gives 23 g. N-methyl-N’-(纬-aminopropyl)piperazine (VIII), b_0.3 52掳. Adding 22 g. VIII to 20 g. cis-螖⁴-tetrahydrophthalic anhydride causes an exothermic reaction; the mixture, heated 2 hrs. at 170-90掳, gives 33 g. N-(纬-tetrahydrophthalimido)propyl-N’-methyl-piperazine (IX), b_0.2 160-5掳 [di-HCl salt m. 258-9掳 (decomposition)]. Adding slowly 30 g. IX in Et₂O to 15 g. LiAlH₄ in 1 l. Et₂O and stirring the solution several hrs. give 2-[N-methyl-N’-(纬-piperazinopropyl)]-I, b_0.1 136-42掳 [tri-HCl salt, m. 270-1掳 (decomposition); trisquaternary methonium salt m. 217-18掳]. In the experiment, the researchers used many compounds, for example, Octahydro-1H-isoindole (cas: 21850-12-4Quality Control of Octahydro-1H-isoindole).

Octahydro-1H-isoindole (cas: 21850-12-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Quality Control of Octahydro-1H-isoindole

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

Synthesis of chirally deuteriated (S-adenosyl-S-methylsulfonio)propylamines and spermidines. Elucidation of the stereochemical course of putrescine aminopropyltransferase (spermidine synthase) was written by Orr, Gary R.;Danz, Deborah W.;Pontoni, Gabriele;Prabhakaran, P. C.;Gould, Steven J.;Coward, James K.. And the article was included in Journal of the American Chemical Society in 1988.SDS of cas: 3130-75-4 This article mentions the following:

The stereochem. course of enzyme-catalyzed aminopropyl transfer was investigated. The stereospecific synthesis of chirally deuteriated (S-adenosyl-S-methylsulfonio)propylamines and several chirally deuteriated spermidine (-)-camphanamide derivatives allowed the elucidation of aminopropyltransferase stereochem. by using ¹H NMR techniques. Putrescine aminopropyltransferase (spermidine synthase) isolated from Escherichia聽coli catalyzed the synthesis of chirally deuteriated spermidines from 1,4-diaminobutane (putrescine) and chirally deuteriated (S-adenosyl-S-methylsulfonio)propylamines. Derivatization of the biosynthetic spermidines to 1,8-bis-(tert-butoxycarbonyl)spermidine (-)-camphanamides and comparison of their ¹H NMR spectra with those of the synthetic standards permits determination of the absolute configuration of the biosynthetic products. The results show that the reaction catalyzed by E. coli spermidine synthase proceeds with inversion of configuration at the methylene carbon undergoing nucleophilic attack by putrescine. These data support a single-displacement mechanism proceeding via a ternary complex of enzyme and both substrates. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4SDS of cas: 3130-75-4).

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.SDS of cas: 3130-75-4

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

A novel method for synthesis of tetrahydro-2H-oxazolo[2,3-a]isoquinolines was written by Dinesha, H. E.;Sandhya, N. C.;Mantelingu, K.. And the article was included in Asian Journal of Chemistry in 2019.Application of 16502-01-5 This article mentions the following:

An efficient and direct method for the synthesis of tetrahydro-2H-oxazolo[2,3-a]isoquinolines I [R = H, 6-OMe; R¹ = H, Me, Ph; R² = H, 4-Me, 2-Br, etc.] was reported. This novel method involved T3P mediated in situ oxidation of benzyl alcs. to aldehyde followed by acetic acid mediated [3 + 2] cycloaddition reaction to afford tetrahydro-2H-oxazolo[2,3-a]isoquinolines I in one-pot operation with good to excellent yields. Heterocyclic alcs. also underwent the reaction with tetrahydroquinolines at room temperature In the experiment, the researchers used many compounds, for example, 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5Application of 16502-01-5).

2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole (cas: 16502-01-5) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Application of 16502-01-5

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

Synthesis of 伪-aminoketones from N-sulfonyl-1,2,3-triazoles via N-sulfinyl imines generated by intramolecular oxygen transfer was written by Xu, Ze-Feng;Shan, Lihong;Zhang, Wan;Cen, Mengjie;Li, Chuan-Ying. And the article was included in Organic Chemistry Frontiers in 2019.Computed Properties of C9H8BrN This article mentions the following:

A general procedure for intramol. oxygen transfer from sulfonyl to a carbenoid carbon was established, extending the reaction mode of the corresponding common N-sulfonyl-1,2,3-triazoles. Indoles, and some other arenes, were employed as nucleophiles to react with the resulting key N-sulfinyl imine intermediate, and valuable 伪-aminoketones could be synthesized conveniently. The synthetic utility of the products was further exhibited by convenient synthesis of gem-diaryl ketones and densely substituted pyrrole. A tentative reaction mechanism was proposed according to control experiments In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methyl-1H-indole (cas: 590417-55-3Computed Properties of C9H8BrN).

4-Bromo-1-methyl-1H-indole (cas: 590417-55-3) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Computed Properties of C9H8BrN

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