Synthesis of New Class of (β-Lactam, Thiazolidinone) Derivatives

Abstract

The reaction of some newly synthesised compound 2, 4-diamino-lH-benz[g]quinolino-5,l0-dione 3-ethyl carboxylate 1 and 2,4-diamino-l ,2,3-trihydropiperpdino[2,3-b]benz[g]-1 ,2,3,4-tetrahydroquinolines-5,6,11-trione 3 ethylcarboxylate 2 with different aromatic aldehyde afforded the corresponding new Schiff bases derivatives 3a-c, 4a-c. The cycloaddition reaction of 3a-c, 4a-c with chloroacetyl chloride and thioglycolic acid give new isolated β -Lactams and thiazlidinone derivatives 5a-c, 7a-c and 6a-c, 8a-c. Compound 1, 2 undergo hydrolysis by NaOH to give carboxylic compound 9,10 which react with different aromatic aldehyde to give new Schiff bases 11a-c and 12a-c. The cycloaddition reaction of 11a-c, 12a-c with chloroacetylchloride and/or mercaptoacetic acid to give 13a-c, 15a-c and 14a-c, 16a-c.

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“…Tables I, II). The activity of the azamethine center in compound 6a-c is more available than the activity of the NH group toward the addition process of chloroacetyl chloride, and this mentioned phenomena is due to the presence of π electron, which makes the foundation of the δ positive and δ negative charge on the carbon and nitrogen atom, respectively, more easy than the presence of this phenomena on the NH group in which the bonding between nitrogen and hydrogen wheather strong according to the nature of this bonding which leads to decreasing of the mobility desire of the hydrogen atom of this pH group 17 . Thus compound 6a-c reacted with chloroacetyl chloride or mercaptoacetic acid to give spiro β-Lactam and spiro thiazolidinone compound 17 7ac and 8a-c.…”

Synthesis of some new spirocyclic β-lactam and spirocyclic thiazolidin-4-one derivatives

“…The mass spectrum of 7'-(4-amino-3-cyano-5,10-dioxo-1,5,10,10a-tetrahydrobenzo[g]quinolin-2-yl)-3-chloro-1-(4-(dimethylamino)phenyl)-3',4,5'-trioxo-3',5'-dihydrospiro-[azetidine-2,2'-thiazolo[3,2-a]pyrimidine]-6'-carbonitrile (7c), taken as a representative example, recorded the molecular ion peak [M] + at m/z 650 (based on 35 Cl) and m/z 652 (based on 37 Cl) which corresponds to C31H19ClN8O5S. Its IR spectrum showed no absorption band due to the exocyclic C=N which appeared for compound 6c at 1644 cm -1 .…”

“…Considering all of these benefits and in pursuance to our interest [33][34][35] in the chemistry of polyfunctional heterocycles with enhanced biological potency, it is very interesting to synthesize new compounds which accommodate the biologically active quinoline, spirocyclic β-lactam and/or spirocyclic thiazolidin-4-one moieties, in the same structure. …”

Benzo[g]quinoline heterocyclic derivative as a typical precursor in the synthesis of new class of cyanine-like dyes

“…This is due to the fact that quinone derivatives are widely used as fungicides [1,2] and antibacterial agents [2][3][4]. Also a large number of chemicals derived from quinone as the basic subunit exhibit prominent pharmacological applications such as antimalarial [5] and herbicidal activity [6].…”