1009-27-4 | - Indole Building Blocks

Swaminathan, S.’s team published research in Indian Journal of Chemistry in 1964 | CAS: 1009-27-4

Indian Journal of Chemistry published new progress in CAplus about 1009-27-4, 1009-27-4 belongs to class indole-building-block, name is 2-Ethoxy-1H-indole, and the molecular formula is C10H11NO, Recommanded Product: 2-Ethoxy-1H-indole.

Swaminathan, S. published the artcileSynthesis of ethyl 1-acetyl-2-(3-indolylmethyl)carbazate. An analog of Nα-acetyltryptophan ethyl ester, Recommanded Product: 2-Ethoxy-1H-indole, the main research area is .

Indole-3-carboxaldehyde (5 g.) in 100 ml. EtOH was added to a solution of 2.69 g. NH2NHAc in 10 ml. H2O containing 1 drop HOAc, and the mixture refluxed 2 hrs. to yield 4.5 g. 3-indolealdehyde acetohydrazone (I), m. 253-5° (EtOH). I (1 g.) in 150 ml. EtOH was hydrogenated 2.5 hrs. at 50 psi over Pd-BaCO3 to yield 0.75 g. 1-acetyl-2-(3-indolylmethyl)hydrazine (II), m. 147.5-8.5° (EtOAc-petr. ether). Et3N (1 g.) in 10 ml. C6H6 was added to a solution of 1 g. II in 100 ml. C6H6, followed by dropwise addition during 30 min. of a solution of 0.6 g. ClCO2Et in 29 ml. C6H6, and the mixture stirred 3 hrs., kept overnight, and worked up to yield 1.1 g. Et 1-acetyl-2-(3-indolylmethyl)carbazate (III), m. 91-2° (C6H6). III was of interest as a potential tryptophan antagonist. A mixture of 0.5 g. II in 20 ml. 40% alc. NaOH was refluxed 6 hrs., EtOH removed in vacuo, and the residue diluted with H2O to yield 0.275 g. 3-indolealdazine (IV), m.p. and mixed m.p. 310-12°. IV (0.5 g.) was also obtained by refluxing 1 g. I with 40 ml. 20% alc. NaOH. A mixture of 1.5 g. indole-3-aldehyde, 0.5 g. 98-100% N2H4.H2O, 10 ml. EtOH, and a drop HOAc was refluxed 1 hr. and cooled to yield 1.2 g. IV, m. 310-12° (Me2CO).

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

Golovko, T. V.’s team published research in Russian Chemical Bulletin in 2008-01-31 | CAS: 1009-27-4

Russian Chemical Bulletin published new progress about Condensation reaction. 1009-27-4 belongs to class indole-building-block, name is 2-Ethoxy-1H-indole, and the molecular formula is C10H11NO, Category: indole-building-block.

Golovko, T. V. published the artcileNew synthesis of pyrido[4,3-b]indoles (γ-carbolines) on the basis of indolin-2-one lactim ether, Category: indole-building-block, the main research area is indolinone lactim ether malononitrile condensation; oxindole lactim ether malononitrile condensation; pyridoindole preparation; gamma carboline preparation; pyrimidocarboline preparation.

Condensation of indolin-2-one (oxindole) lactim ether with H2C(CN)2 leads to 2-dicyanomethylidene-2,3-dihydroindole. Subsequent reaction with DMF di-Et acetal [or HC(OEt)3] and further cyclization affords 4-cyanopyrido[4,3-b]indoles (γ-carbolines). 3-Amino-4-cyanopyrido[4,3-b]indole was used in the synthesis of substituted pyrimido[4,5-c]-γ-carbolines.

Dobrowolski, P.’s team published research in Journal of Molecular Structure in 1987-09-30 | CAS: 1009-27-4

Journal of Molecular Structure published new progress about NMR (nuclear magnetic resonance). 1009-27-4 belongs to class indole-building-block, name is 2-Ethoxy-1H-indole, and the molecular formula is C10H11NO, Application In Synthesis of 1009-27-4.

Dobrowolski, P. published the artcileProton and carbon-13 NMR study of the prototropic equilibriums of 2-indolinone, Application In Synthesis of 1009-27-4, the main research area is NMR indolinone tautomerism.

13C NMR data are reported for 0.5 M CDCl3 solutions of 2-indolinone and six related compounds The question of prototropic equilibrium is discussed involving three possible tautomers, A, B, C. Form A is found to predominate in the dynamic equilibrium established for three of the compounds studied. In the case of a fourth compound slow exchange between forms B and C results in the finding of both of these forms in the approx. ratio 1:1.8. These findings are supported by 1H NMR measurements. Corresponding 1H and 13C NMR measurements on methanol solutions are essentially the same.

Kamienski, Bohdan’s team published research in Bulletin of the Polish Academy of Sciences, Chemistry in 1989-12-31 | CAS: 1009-27-4

Bulletin of the Polish Academy of Sciences, Chemistry published new progress about NMR (nuclear magnetic resonance). 1009-27-4 belongs to class indole-building-block, name is 2-Ethoxy-1H-indole, and the molecular formula is C10H11NO, SDS of cas: 1009-27-4.

Kamienski, Bohdan published the artcileA multinuclear NMR study of the tautomeric equilibria of some indolinones, SDS of cas: 1009-27-4, the main research area is NMR indolinone tautomerism.

1H, 13C and 15N NMR data are reported for three indolinones which, in principle, may exhibit tautomeric equilibrium together with the corresponding NMR results for three model compounds It is found that when taken together the 1H, 13C and 15N NMR results provide a greater insight into both fast and slow exchange equilibrium than would either of these techniques considered alone. The results are indicative of the dependence of equilibrium upon the choice of solvent.

Varlet, Thomas’s team published research in Journal of the American Chemical Society in 2021-08-04 | CAS: 1009-27-4

Journal of the American Chemical Society published new progress about [4+2] Cycloaddition reaction. 1009-27-4 belongs to class indole-building-block, name is 2-Ethoxy-1H-indole, and the molecular formula is C10H11NO, Recommanded Product: 2-Ethoxy-1H-indole.

Varlet, Thomas published the artcileEnantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition, Recommanded Product: 2-Ethoxy-1H-indole, the main research area is spiroindolenine preparation diastereoselective enantioselective; indolylmethanol dienecarbamate cycloaddition chiral phosphoric acid catalyst.

A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates. Modular access to two different diastereoisomers with high enantioselectivities was obtained by careful choice of reaction conditions. Their functional group manipulation provides an efficient access to enantioenriched spirocyclohexyl-indolines and -oxindoles. The origins of this stereocontrol have been identified using DFT calculations, which reveal an unexpected mechanism compared to previous work dealing with enecarbamates.