A Convenient Synthesis of 7-Halo-1-indanones and 8-Halo-1-tetralones

Abstract

A regioselective oxidation of N-indan-4-yl-acetamide or N-(5,6,7,8-tetrahydronaphthalen-1-yl)acetamide with potassium permanganate followed by acidic hydrolysis gave 7-aminoindan-1-one or 8-aminotetral-1-one in good yield. The amino ketones were converted to the corresponding 7-haloindanone or the 8-halotetralone. Another method to prepare 7-haloindan-1-ones was completed by a cyclization of 3-chloro-1-(2-halophenyl)propan-1-one under Friedel-Crafts conditions to produce the product in gram quantity.

New Monocyclic, Bicyclic, and Tricyclic Ethynylcyanodienones as Activators of the Keap1/Nrf2/ARE Pathway and Inhibitors of Inducible Nitric Oxide Synthase

“…Unexpectedly, a previously reported method 25 for conversion of 7-amino-1-indanone (74) to 76 using CuCl 2 and t-BuNO 2 in CH 3 CN gave 76 in much lower yield (15%) than the reported yield (64%), with N-(3-oxo-2,3-dihydro-1H-inden-4-yl)acetamide (75) as the major (side) product. 28 However, we could obtain 76 in 86% yield by the traditional Sandmeyer reaction conditions (diazotization and subsequent chlorination with CuCl under acidic conditions).…”

“…Chloro-and bromotricyclic ethynylcyanodienones 11 and 12 were synthesized in 11 steps from 8-chloro-and 8-bromo-1-tetralone (61 and 64) 25 …”

Preparation of phenalenes and hydronaphthacenes through tandem alkyne Fischer–carbene complex coupling and inter- or intra-molecular Diels–Alder reactions

“…Alkynyltetralone 1 was prepared from 1-amino-5,6,7,8-tetrahydronaphthalene via the known transformation to 8-bromo-1-tetralone 14 followed by Sonogashira coupling. This method, though lengthy, is superior to the alternative preparation of 8-bromo-1-tetralone from α-tetralol, 15 since the ortho-metallation process would never go to completion and separation of tetralol and bromotetralol was quite difficult.…”

“…The five-membered ring analog 3 was prepared from 2-bromobenzoyl chloride using the Nazarov cyclization as a key step. 14 The bis(alkyne) derivative 5 was synthesized from 1,3-dibromobenzene through regioselective lithiation, 16 followed by formylation and double Sonogashira coupling.…”

A Flexible Strategy Towards Thienyl‐, Oxazolyl‐ and Pyridyl‐Fused Fluorenones

“…8-Bromotetralone was prepared according to Nguyen et al [28] UV/Vis analyses were performed with a Perkin-Elmer spectrophotometer UV/Vis/NIR Lambda 19; quartz cells (1 cm path) were used for the measurements. Petroleum ether was distilled under Argon.…”