Some reactions of 4-chloro and 4-hydrazino 2- [naphthylmethyl] quinazoline

ABSTRACT

The considerable biological and medicinal activities of quinazoline derivatives as anti-inflammatory[1], antihypertensive[2] hypnotic[3] anti-adrenergic[4] and as fungicides[5] have stimulated the recent interest in the synthesis of derivatives of these ring systems. In continuation of our previous work [6] we have investigated a variety of synthetic routes to a number of quinazoline derivatives. Thus, we have found that the reaction of 4-chloro-2- [a-naphthylmethyl]-quinazoline [1] with aniline, benzylamine, and hydrazine hydrate in boiling butanol gives the corresponding 4-[anilino, benzylamino and hydrazino]-2- [alpha -naphthyl methyl]-quinazolines [2a-c]. However, treatment of [1] with sodium azide in boiling acetic acid gave the corresponding tetrazoloquinazoline derivatives[3]. Refluxing of [1] with acylhdrazines, namely cyanoacetyl hydrazine and benzoylhydrazine in boiling butanol gave the corresponding 3-[cyanomethyl or phenyl]-triazolo [3,4-a]-5 [alpha -naphthyl methyl]-quinazoline [4a and b]. In a recent series of publications [7,8], it has been reported that, the reaction of 4-chloroquinazoline with amino acids gave imidazo quinazoline derivatives. In the present investigation, the reaction of [1] with glycine in boiling butanol and the ring closure by Ac[2]O yielding 5-oxo-imidazo [3,4-a] -2- [[alpha -naphthyl methyl]-quinazoline [5]. Recently [6,9], It has been proved that 4-chloro-quinazoline is a useful precursor in the synthesis of fused nitrogen bridged benzopyrimidinoquinazoline. Similarly, we found that treatment of [1] with anthranilic acid in boiling butanol gave benzopyrimidinoquinazoline [6]