ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 GRIGNARD 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19690520817
Permalink