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Die Aminoalkylierung von Chinazolinen und Chinazolonen mit Hilfe der G RIGNARD ‐Reaktion. 5. Mitteilung über G RIGNARD ‐Reaktionen mit Halogenalkyliminen [2]
Author(s) -
Marxer A.,
Salzmann U.,
Hofer F.
Publication year - 1969
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19690520817
Subject(s) - chemistry , quinazoline , yield (engineering) , medicinal chemistry , alkyl , aryl , chloride , stereochemistry , organic chemistry , materials science , metallurgy
Quinazoline is aminoalkylated at C(4) by 3‐dimethylaminopropyl‐magnesium‐chloride in preparative yield to give 3 , and by oxidation 5 , just as aryl and alkyl‐magnesiumbromide give 15 , 19 , and 22 . These 4‐substituted quinazolines yield by further treatment with the same G RIGNARD compound by 3, 4 or 1, 2‐addition 3, 4‐di‐hydro‐quinazolines ( 12 , 16 ) and 1, 2‐dihydro‐quinazolines ( 13 , 17 , 20 , 23 ), the latter being formed exclusively when the 4‐position in the quinazoline is occupied by bulky residues; only the later can be oxidised to give 2,4‐disubstituted aromates (cf 14 , 18 , 21 , 24 ). The spectroscopic and physicochemical behaviour of the dihydro compounds and the aromatic and the aromatic compounds are discussed.