Synthesis and Characterization of Indazol-3-one and Thioxo Pyrimidines Derivatives from Mono and Twin Chalcones

Abstract

This work involved synthesis and characterization of new mono and twin fused pyrazolone(indazol-3-one) (IV) a-d and thioxo pyrimidine (III) a-d derivatives from Chalcones (mono(I) a,b and twin(I) c,d ) The synthesis of mono chalcones (I) a,b includes the reaction of (p-methoxy or p-methyl) benzaldehyde with 4-amino acetophenone while the twin acetophenone with p-methoxy benzaldehyde to produce twin chalcones (I) c,d , then converted it by Robinson annulations reaction to form the corresponding derivatives (II) a-d afterward reflux the cyclohexenones with hydrazine and some drops of GAA lead to form indazole derivatives (IV) a-d . Pyrimidines were synthesized via the reaction of chalcones with thiourea in NaOH and 80% ethanol. All these compounds are characterized by FT-IR spectroscopy and some of them by 1 HNMR spectroscopy.

Synthesis of Some Novel Nanosized Chelates of Anchoring Bisazo Dye 5-[5-(4,6-Dioxo-2-thioxo-hexahydro-pyrimidin-5-ylazo)-naphthalen-1-ylazo]-2-mercapto-1H-pyrimidine-4,6-dione and Their Applications as Antioxidant and Antitumor Agents

“…32 The spectrum also gave a band at 1639 cm −1 attributed to υ(CN) group of the thiobarbituric moiety. 33 The observed bands at 3094, 1520, and 788 cm −1 were attributable to ν, δ, and γ of the amidic NH group, respectively. 34 The azo group was assigned by the appearance of bands at 1422 and 1411 cm −1 due to υ(NN).…”

“… , The (SH) group was characterized by the observed band at 2594 cm –1 attributed to υ­(SH), additional bands at 625 and 580 cm –1 due to overlapped bands of υ­[(C–S) + (N–CO)] and [υ­(N–CO) + (SH deformation)], respectively. − However, the 720 cm –1 band was assigned to υ­(CS) with other bands at 1178 and 1064 cm –1 characterized to υ­(C–N) + υ­(CS) . The spectrum also gave a band at 1639 cm –1 attributed to υ­(CN) group of the thiobarbituric moiety . The observed bands at 3094, 1520, and 788 cm –1 were attributable to ν, δ, and γ of the amidic NH group, respectively…”

Synthesis of New Oxopyrimidine and Cyanopyridine Derivatives Containing the Pyrimidine Benzothiazole Moiety with the Evaluating their Colon Anticancer Bioactivity

“…The 1 H NMR spectrum of compound A14 showed a signal at 11.20 ppm that belongs to the NH, which is good evidence for the formation of compound A14. The 13 C NMR spectrum displayed a new signal at 176.8 ppm of the carbonyl group for the new oxopyrimidine ring [21,22]. The nicotinonitrile derivatives A16-A21 were synthesised by Michael's addition from the reaction of the abovementioned chalcones A4-A9 with malononitrile.…”

Design and Synthesis of Novel Bis Thiazolo[4,5-c]Isoxazolines Bearing 1,2,4-triazole Ring Derived From the Related 4-thiazolidinons as Antimicrobial Agents

“…Following a review of the literature, many novel isoxazoline derivatives were synthesized using various techniques. However, novel isoxazoline compounds were produced by 1,3-dipolar cycloaddition of nitrile oxides with dialkyl maleate [13,14]. In contrast, chalcones have been used to produce a number of novel mono-and twin-fused pyrazolone (indazol-3-one) and thioxopyrimidine derivatives [15].…”