23240-52-0

Basic information

• Product Name: 2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE OXIME
• Synonyms: 2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE OXIME
• CAS NO: 23240-52-0
• Molecular Formula: C12H12N2O
• Molecular Weight: 200.24
• Mol File: 23240-52-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE OXIME(23240-52-0)
• EPA Substance Registry System: 2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE OXIME(23240-52-0)

Safety Data

• Hazardous Substances Data: 23240-52-0(Hazardous Substances Data)

Upstream product

• 3456-99-3 1-oxo-2,3,4,9-tetrahydrocarbazole 

Relevant articles and documents

Regioselective synthesis of heterocycles containing nitrogen neighboring an aromatic ring by reductive ring expansion using diisobutylaluminum hydride and studies on the reaction mechanism

(Chemical Equation Presented) A systematic investigation of the reductive ring-expansion reaction of cyclic ketoximes fused to aromatic ringswith diisobutylaluminum hydride (DIBALH) is described. This reaction regioselectively afforded a variety of five- to eight-membered bicyclic heterocycles or tricyclic heterocycles containing nitrogen neighboring an aromatic ring, including indoline, 1,2,3,4,5,6-hexahydrobenz[b]azocine, 3,4-dihydro-2H-benzo[b] [1,4]oxazine, 2,3,4,5-tetrahydrobenzo[b][1,4]thiazepine, 1,2,3,4,5,6- hexahydroazepino[3,2-b]-indole, 2,3,4,5-tetrahydro-1H-benzothieno[2,3-b]azepine, 2,3,4,5-tetrahydro-1H-benzothieno[3,2-b]-azepine, 5,6-dihydrophenanthridine, and 5,6,11,12-tetrahydrodibenz[b, f]azocine. The reaction mechanism leading to the rearrangement was investigated on the basis of the restricted Becke three-parameter plus Lee-Yang-Parr (B3LYP) density functional theory (DFT) with the 6-31G (d) basis set. It was found that the reaction proceeds through a three-centered transition state via a stepwise mechanism because the potential energy curve along the intrinsic reaction coordinate (IRC) had twomaxima (saddle points; TS1 and TS2) and the partial phenonium cation intermediate C. In addition to cyclic ketoximes fused to aromatic rings, the reactions of various cyclic and acyclic ketoximeswere examined to investigate preference of migrating group. It was found that themore electron-rich group migrated preferentially to give the corresponding secondary amines.

Synthesis of Novel 3-Acetyl-2-hydroxy-1-N,N-diacetylaminocarbazole Derivatives

The synthesis of hitherto unknown 3-acetyl-2-hydroxy-1-N,N-diacetylaminocarbazole (3a-f), is reported.The hydroxyiminocarbazoles (2a-f), prepared from 1-oxo-1,2,3,4-tetrahydrocarbazoles (1a-f) on treatment with acetyl chloride in acetic anhydride yielded the title compounds (3a-f). - Keywords: 1-Hydroxyimino-1,2,3,4-tetrahydrocarbazoles, 3-Acetyl-2-hydroxy-1-N,N-diacetylaminocarbazoles, Aromatization, Thermal Fries Rearrangement, Antimicrobial Activities