62084-97-3Relevant academic research and scientific papers
Experiments towards the Preparation of 6-Hydroxy-, 6-Methoxy-, and 6-(Hydroxyphenyl)-2,3-dihydro-1,4-diazepinium Salts and 1,2-Dihydro-5-(hydroxyphenyl)-2-oxopyrimidinium Salts
Lloyd, Douglas,Reichardt, Christian,Struthers, Margot
, p. 1368 - 1379 (2007/10/02)
The preparation of a number of 2,3-dihydro-6-(hydroxyphenyl)-1,4-diazepinium salts (11c-f) and of 1,2-dihydro-5-(hydroxyphenyl)-2-oxopyrimidinium salts (17a, b) from 3-(hydroxyphenyl)vinamidinium salts (10b,c) is described.Attempted preparation of a 3-(2-
Diazepines. Part 25. Preparation and Properties of 6-Aryl-2,3-dihydro-1,4-diazepinium Salts. Electronic Interaction between the Rings and Steric Inhibition thereof
Lloyd, Douglas,Tucker, Kanwaljit S.,Marshall, Donald R.
, p. 726 - 735 (2007/10/02)
A variety of 6-aryldihydrodiazepinium salts (including also 6-biphenyl-4-yl, 6-α-naphthyl, and 6-N-pyridyl) has been prepared, mostly by reactions of 1,2-diamines with 3-aryl-1,5-diazapentadienium salts.The electron-rich dihydrodiazepinium cation activates the 6-aryl substituent towards electrophilic attack, and halogenation and nitration take place at the p-position.Substituents vicinal to the ring junction in either the six- or seven-membered rings inhibit this reactivity, presumably by preventing coplanarity of the two rings; the 13C n.m.r. spectra of these vicinally substituted compounds also show the lowered electronic interactions between the rings.NN'-diphenyl and NN'-dibenzyl substituents also inhibit electrophilic substitution in the 6-phenyl ring.Solution in deuteriosulphuric acid generates a stable radical species.Nucleophiles (monoamines, diamines, sodium hydroxide) attack the 5- and 7-positions of the diazepine ring.The 13C n.m.r. and mass spectra of these compounds are discussed.
