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

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]

Synthesis of pyrimidine derivatives via the reduction of Schiff base type intermediates

Reactions of 5-formyl derivatives of uracil, 4-thiouracil and 2', 3',-0-isopropylideneuridine with glucosamine via Schiff base intermediate have been described. The antimicrobial activity of the prepared compounds has been also studied

Study on the stability and behaviour of 2-benzamido [alpha-naphthylidene] methyl-4- [3H] quinazolinone

The aminolysis of 2-benzamide [alpha-naphthylidene]-4H-3,1- benzoxazine-4-one 1 gave 2-benzamide, [alpha-naphthylidene]-4-[3H]- quinazolinone 2. The chlorination, benzoylation and Mannich reaction of 2 have been studied. Also, the behavior of 4-chloroquinazoline 4 towards acylhydrazides, sodium azide, alkylating agents, active methylene compounds and amino acid have been described

Synthesis and some reactions of 8-tert-butyl-6-hydroxy-4-methyl coumarin

The synthesis of 8-tert-butyl-6-hydroxy-4-methyl coumarin 2 was described. The nitration of compound 2 followed by reduction gave the amino coumarin derivative 5. The latter compound condensed with acetic acid in presence of P2O5 to give the benzoxazole derivative 6. Also, the compound 5 reacted with CS2 in presence of KOH/CH3OH to afford the benzoxazole-2-thione derivative 7. It has been found that the coumarin derivative 2 reacted with Grignard reagent by 1, 4 addition to give the products 8a,b

Studies on beta-lactans and thiazolidinones: part III: synthesis and biological activity of some new selena diazolyl-azetidin-2-ones and thiazolidin-4-ones

P-aminoacetophenone was smoothly condensed with semicarbazide to produce the corresponding semicarbazone [1]. The latter compound was oxidized with SeO 2 to give 4-[p-aminophenyl-4-yl]-1, 2, 3- selenadiazole [II]. Compound [II] was allowed to react with aromatic aldehydes to afford the corresponding Schiff bases [III]. Cyclocondensation of mercaptoacetic acid and chloro- acetyl chloride with compound [III] to give thiazolidinones [IV] and azetidinones [V], respectively. The constitution of some of the prepared products is discussed through their microanalysis and infrared spectra. The biological activities of some of these compounds were tested