Reaction of 2-R 5-Oxo 5-H 6- Ethylcarboxylate 7-Phenyl-[1,3,4]Thiadiazolo-[3,2-A]Pyrimidine with Morpholin and their Properties

Abstract

this article presents Synthesis of 2-R5-oxo 5-H 6 -Carbomorpholin 7-phenyl 1,3,4-thiadiazolo-[3,2-a] pyrimidine through reaction of 2- R 5 - Oxo 5 - H 6- EthylCarboxilate 7 – phenyl -1, 3,4 – Thiadiazolo-[3,2-a] pyrimidine with morpholin. in particular,for the new antibacterial drugs in these homologousseries of compounds, we have synthesized 2-R5-oxo 5-H 6 -Carbomorpholin 7-phenyl 1,3,4-thiadiazolo-[3,2-a] pyrimidine .The structures of the compounds obtained are set NMR, ¹³C, IR- spectroscopy.

The diverse and interesting biological activity of thiadiazoleshas been reported ^1-4It is well known that these heterocyclesare valuable building blocks. Many methods for preparationof these heterocyclic ring systems and their fusedanalogues have been described in the literature ^5-6. 1,3,4-thiadiazoles provided a usefulmethod for the synthesis of thiadiazolopyrimidine ⁷.Pyrimidine derivatives have been found to be associated with diverse biological activities and numerous reportshave appeared in the literature ^8-12. This highlighted their chemistry and use. The pyrimidine derivatives haveremarkable pharmacological activity ^13,14 and widely used in the field of anti-microbial, antiviral, etc. Thiadiazole derivatives were shown to possess many biological activities including anti-inflammatory ^15-16.TheThe introduction of a substituent at position 6 of the1,3,4-thiadiazolo [3,2-a] pyrimidine system efficientlyenhances the physiological activity of the molecule^17-19. This replacement occurs in the reactions of 1,3,4 -thiadiazolo [3,2-a] pyrimidine derivatives withelectrophiles^20,21.Derivatives of 1,3,4-thiadiazolo [3,2-alpyrimidine are potential biologically active substances,^22-25 The introductionof ketene dithioacetal fragments into the moleculesmakes it possible to synthesize heterocyclic systemswith various functional groups^26,27.We Preparated2-R5-oxo 5-H 6 -Carbomorpholin 7-phenyl 1,3,4-thiadiazolo-[3,2-a] pyrimidine in two stage. In step first we have synthesize2-R5-oxo5-H6-EthylCarboxilate7-phenyl 1,3,4-thiadiazolo[3,2,-a]pyrimidine(3) with use2- R 5-amino 1,3,4- thiadiazole(1) andethyl 2- formyl 3- oxo 3- phenyl propanoate (2 )(Figure 1).

Table 1.synthesisof2- R 5-oxo5-H6-Carbomorpholin 7-phenyl -1,3,4-thiadiazolo [3,2-a] pyrimidinefrom 2- R5-oxo5-H6-ethylcarboxylate7-phenyl1 ,3,4- thiadiazolo [3,2-a] pyrimidineand morpholina

In another stage 2-R5-Oxo5-H6-EthylCarboxilate7-phenyl 1,3,4-thiadiazolo-[3,2,-a]pyrimidinereacted with morpholin(4) until produced 2-R 5-oxo 5-H 6 –Carbomorpholin 7 -phenyl 1,3,4-thiadiazolo-[3,2-a] pyrimidine(5-9)(f2).

http://www.orientjchem.org/wp-content/uploads/2014/04/Vol30_No1_React_Reza_fig1.jpg

Result and Discussion

we tried synthesisof 2- R 5-oxo 5-H 6-Carbomorpholin 7-phenyl -1,3,4-thiadiazolo [3,2-a] pyrimidinewith 2-R 5-oxo 5-H 6-ethylcarboxylate 7-phenyl 1 ,3,4-thiadiazolo [3,2-a] pyrimidine and morpholin in varioussolvent. But alcohols are the best solvents to this reaction .The alcoholssuch asmethanolandethanolalcoholhave more use. The herbicidal activities of the target compounds were evaluatedagainst a variety of weeds by flat-utensil method accordingwith the standard bioactivity test.Applicability of this procedures, that we synthesis a wide variety of 2-R 5-oxo 5-H 6-R-amide derivatives7-phenyl 1 ,3,4- thiadiazolo [3,2-a] pyrimidine from 2-R 5-oxo 5-H 6- ethyl carboxylate7-phenyl 1,3,4-thiadiazolo [3,2- a]pyrimidine and morpholinin the presence of alcohol ethanol at 78 ^oC and obtained the desirable products in good to excellent yields (Table 1).

Table 1.synthesisof2- R 5-oxo5-H6-Carbomorpholin 7-phenyl -1,3,4-thiadiazolo [3,2-a] pyrimidinefrom 2- R5-oxo5-H6-ethylcarboxylate7-phenyl1 ,3,4- thiadiazolo [3,2-a] pyrimidineand morpholina

Experimental

A mixture of 2-CH₃ 5-oxo 5-H 6-ethylcarboxylate 7-phenyl 1,3,4- thiadiazolo [3,2-a] pyrimidine (1 mmol),amin derivatives(1 mmol) was stirred magnetically at 78^oC and the progress of the reaction was monitored by thin-layer chromatography (TLC). The reaction mixture was filtered.In all the cases, the product obtained after the usual work up gave satisfactory spectral data.For example,2-CH₃ 5-oxo 5-H 6-ethylcarboxylate 7-phenyl 1,3,4- thiadiazolo [3,2-a] pyrimidine (1 mmol-0.315gr),morpholin(1 mmol- 0.087gr)reacted to gether in alcoholethanol at 78 ^oC.Andtheproduct( 2-CH₃ 5-oxo 5-H 6-carbomorpholin 7-phenyl 1,3,4- thiadiazolo [3,2-a] pyrimidine )isobtainedin 85%yield.2-CH₃ 5-oxo 5-H 6-carbomorpholin 7-phenyl -1,3,4-thiadiazolo [3,2-a] pyrimidine:¹H NMR (400 MHz, CDCl₃, δ ppm): 0.9(s,3H,CH₃ ););3.65(t,2H,CH₂);7.30-7.46 (5H, Ph); – ¹³C NMR (100 MHz, CDCl₃, δ ppm): 24.2(CH₃),45.5 (CH₂),45.5 (CH₂),66.2 (CH₂), 66.2 (CH₂), 118 (C), 126,4 (CH) , 126,4 (CH) ,128(CH), 128.7(CH), 128.7(CH), 136.9(C), 154.7(C), 159 .8(C),162.1(C), 163 (C),168(C).

Conclusions

Compound 2- R 5-oxo 5-H 6-Carbomorpholin 7-phenyl -1,3,4-thiadiazolo [3,2-a] pyrimidine were procedure in excellent yields from 2- R 5-oxo 5-H 6-ethylcarboxylate 7-phenyl 1,3,4- thiadiazolo [3,2-a] pyrimidine and morpholinthat have a broadspectrum of antimicrobial activity .The pyrimidine derivatives haveremarkable pharmacological activity and widelyused in the field of anti-microbial, antiviral. Such medicinal utilities of the Pyrimidine derivatives prompted to synthesize the new pyrimidinethiosemicarbazide,1,3,4-thiadiazole compounds.

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