41978-91-0

Upstream product

• 83-34-1 3-Methylindole 

Downstream Products

• 114642-81-8 3-methylindole-2-azo-(4'-nitrobenzene) 

Relevant academic research and scientific papers

Evidence supporting the formation of 2,3-epoxy-3-methylindoline: A reactive intermediate of the pneumotoxin 3-methylindole

The existence of a cytochrome P450-dependent 2,3-epoxide of the potent pneumotoxin 3-methylindole was indirectly confirmed using stable isotope techniques and mass spectrometry. Determination of hydride shift and incorporation of labeled oxygen in 3-methyloxindole and 3-hydroxy-3- methyloxindole, metabolites that may be in part dependent on the presence of the epoxide, were utilized as indicators of the epoxide's existence. One mechanism for the formation of 3-methyloxindole involves cytochrome P450- mediated epoxidation followed by ring opening requiring a hydride shift from C-2 to C-3. Through incubations of goat lung microsomes with [2-2H]-3- methylindole, the retention of 2H in 3-methyloxindole was found to be 81%, indicating a majority of the oxindole was produced by the mechanism described above. 3-Hydroxy-3-methylindolenine is an imine reactive intermediate that could be produced by ring opening of the 2,3-epoxide. The imine may be oxidized to 3-hydroxy-3-methyloxindole by the cytosolic enzyme aldehyde oxidase. Activities of this putative detoxification enzyme were determined in both hepatic and pulmonary tissues from goats, rats, mice, and rabbits, but the activities could not be correlated to the relative susceptibilities of the four species to 3-methylindole toxicity. The 18O incorporation into either 3-methyloxindole or 3-hydroxy-3 methyloxindole from both 18O2 and H2/18O was determined. The 18O incorporation into 3-methyloxindole from 18O2 was 91%, strongly implicating a mechanism requiring cytochrome P450- mediated oxygenation. Incorporation of 18O into 3-hydroxy-3-methyloxindole indicated that the alcohol oxygen originated from molecular oxygen, also implicating an epoxide precursor. These studies demonstrate the existence of two new reactive intermediates of 3-methylindole and describe the mechanisms of their formation and fate.

Two-in-One Strategy for Palladium-Catalyzed C?H Functionalization in Water

Transition metal catalyzed C?H functionalizations have been developed as powerful methods for C?C bond formations. Directing groups, removable directing groups, traceless directing groups, and transient directing groups (TDGs) have been successfully used to improve the reaction efficiencies. For the development of greener and more sustainable methods, C?H functionalization using a TDG that also serves as a reagent in aqueous solvent was investigated. The palladium-catalyzed C?H functionalization of tryptamine derivatives using ketones in water successfully generated tetrahydro-β-carbolines with a quaternary carbon center at C1. Deuterium-labeling experiments are discussed to provide insight into the mechanism. The C2-position of pyridine was also successfully functionalized by this strategy.

Synthesis of a Novel Type of 2,3′-BIMs via Platinum-Catalysed Reaction of Indolylallenes with Indoles

Optimisation, scope and mechanism of the platinum-catalysed addition of indoles to indolylallenes is reported here to give 2,3′-BIMs with a novel core structure very relevant for pharmaceutical industry. The reaction is modulated by the electronic properties of the substituents on both indoles, with the 2,3′-BIMs favoured when electron donating groups are present. Although simple at first, a complex mechanism has been uncovered that explains the different behaviour of these systems with platinum when compared with other metals (e.g. gold). Detailed labelling studies have shown Pt-catalysed 6-endo-trig cyclisation of the indollylallene as the first step of the reaction and the involvement of two cyclic vinyl-platinum intermediates in equilibrium through a platinum carbene, as the key intermediates of the catalytic cycle towards the second nucleophilic attack and formation of the BIMs.

CARBON DIOXIDE: A REAGENT FOR THE PROTECTION OF NUCLEOPHILIC CENTRES AND THE SIMULTANEOUS ACTIVATION TO ELECTROPHILIC ATTACK-PART XII. ONE-POT CONVERSION OF 3-METHYLINDOLE INTO 2-FORMYL-3-METHYLINDOLE

3-Methylindole is converted via treatment of intermediate lithium 2-lithio-3-methylindole-1-carboxylate with demethylformamide or methyl formate, as formylating agent, into 2-formyl-3-methylindole in 54percent overall yield in a one-pot procedure.