Phosphoramides. X. Phosphorus Pentaoxide Amine Mixtures and HMPT as Reagents in the Synthesis of 4-Amino- and 4-Dimethylamino-2,3-polymethylenequinolines.
- 1 January 1979
- journal article
- research article
- Published by Danish Chemical Society in Acta Chemica Scandinavica
- Vol. 33b (5) , 313-318
- https://doi.org/10.3891/acta.chem.scand.33b-0313
Abstract
4-Substituted-2,3-polymethylenequinolines are used as enzyme inhibitors, analeptics, respiratory stimulants and analgetics. 4-Dimethylamino-2,3-polymethylenequinolines 3a-g were prepared by heating appropriate cycloalkanones with methyl anthranilate 1 in HMPT [hexamethylphosphoric triamide] at reflux temperature. 6,12-Bis(dimethylamino)dibenzo[b,f][1,5]diazocine 10 and 2,3,5,6-bis(polymethylene)pyridines 11 were isolated. 4-Amino-2,3-polymethylenequinolines 16a-d were prepared by heating cyclohexanone or cycloheptanone and methyl anthranilates with a phosphorus pentaoxide, diethylamine, and diethylamine hydrochloride reagent system. Using diethylamine or dibutylamine without the corresponding hydrochlorides 11-ethylamino- and 11-butylamino-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinoline 14 were isolated in low yields. In many of the reactions 2,3-polymethylene-4(1H)-quinolinones could be isolated and were presumably reaction intermediates.This publication has 1 reference indexed in Scilit:
- Compounds Acting on the Central Nervous System. IV. 4-Substituted 2,3-PolymethylenequinolinesJournal of Medicinal Chemistry, 1966