Synthesis of Novel Benzofuran‐Gathered C‐2,4,6‐substituted Pyrimidine Derivatives Conjugated by Sulfonyl Chlorides: Orally Bioavailable,Selective, Effective Antioxidants and Antimicrobials Drug Candidates

In the present study, we have made an effort to develop the novel synthetic antioxidants and antimicrobials with improved potency. The novel benzofuran‐gathered C‐2,4,6‐substituted pyrimidine derivatives 5a , 5b , 5c , 5d , 5e , 5f , 6a , 6b , 6c , 6d , 6e , 6f , 7a , 7b , 7c , 7d , 7e , 7f , 8a , 8b , 8c , 8d , 8e , 8f , 9a , 9b , 9c , 9d , 9e , 9f were synthesized by simple and efficient four‐step reaction pathway. Initially, o‐alkyl derivative of salicylaldehyde readily furnish corresponding 2‐acetyl benzofuran 2 in good yield, upon the treatment with potassium tertiary butoxide in the presence of molecular sieves. Further, Claisen–Schmidt condensation with aromatic aldehydes via treatment with thiourea followed by coupling reaction with different sulfonyl chlorides afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, ¹H NMR, ¹³C NMR, mass, and elemental analysis and further screened for their antioxidant and antimicrobial activities. The results showed that the synthesized compounds 8b , 8e , 9b , and 9e produced significant antioxidant activity with 50% inhibitory concentration higher than that of reference, whereas compounds 7d and 7c produced dominant antimicrobial activity at concentrations 1.0 and 0.5 mg/mL compared with standard Gentamicin and Nystatin, respectively.     

Synthesis and Antimicrobial Activities of Novel Series of 3‐(4‐(2‐substituted thiazol‐4‐yl)phenyl)‐2‐(4‐methyl‐2‐substituted thiazol‐5‐yl)thiazolidin‐4‐one Derivatives

In the present investigation, a novel series of 3‐(4‐(2‐substituted thiazol‐4‐yl)phenyl)‐2‐(4‐methyl‐2‐substituted thiazol‐5‐yl)thiazolidin‐4‐one derivatives were synthesized by condensation of 2‐substituted‐4‐methylthiazole‐5‐carbaldehyde with 4‐(2‐substituted thiazol‐4‐yl)benzenamine followed by cyclo‐condensation with thioglycolic acid in toluene. All the newly synthesized compounds were characterized by spectral (IR, ¹H NMR, ¹³C NMR, and Mass) methods. The title compounds were screened for quantitative antibacterial activity (minimal inhibitory concentration). All compounds 7a , 7b , 7c , 7d , 7e , 7f , 7g , 7h and 8a , 8b , 8c , 8d , 8e , 8f , 8g , 8h show moderate to good antimicrobial activity, whereas compounds ( 7a , 7b , 7c , 7d , 7e , 7f , 7g , 7h ) also show moderate antifungal activity.     

Synthesis,characterization, and in vitro biological studies of some novel pyran fused pyrimidone derivatives

A variety of pyrano[2,3‐d]pyrimidine‐5‐one derivatives 5 , 5a , 5b , 5c , 5d , 5e , 5f , 5g , 5h , 5i , 5j , 6 , 6a , 6b , 6c , 6d , 6e , 6f , 6g , 6h , 6i , 6j have been synthesized from 6‐amino‐4‐(substituted phenyl)‐5‐cyano‐3‐methyl‐1‐phenyl‐1,4‐dihydropyrano[2,3‐c]pyrazole derivatives 4a , 4b , 4c , 4d , 4e , 4f , 4g , 4h , 4i , 4j via cyclization using formic acid and acetic acid. All the newly synthesized compounds have been characterized by IR, ¹H NMR, ¹³C NMR, and elemental analysis. All the synthesized compounds have been screened for antibacterial, antifungal and antitubercular activity. J. Heterocyclic Chem., (2012).     

Synthesis of some novel pyrazoline‐thiazole hybrids and their antimicrobial activities

A series of novel thiazolyl pyrazolines 7a‐h , 9a‐f , and 11a‐f have been synthesized by the reaction of thioamide derivatives 5a , b with 1‐aryl‐2‐bromoethanones 6a‐d , chloroacetones 8a‐c , and hydrazonoyl chlorides 10a‐c . Additionally, pyrazoles 15a‐c and 20 were prepared starting from enaminone 13 . These newly synthesized compounds were screened for their in vitro antibacterial activity against four bacterial species. Compound 11b showed a moderate activity against Klebsiella pneumoniae. Compounds 7c and 11c revealed a moderate activity against Pseudomonas aeruginosa. In addition, the antifungal activity of the newly synthesized compounds was determined against five fungal strains. Compounds 7e , 7g , and 11e showed a good activity against Aspergillus flavus and Penicillium expansum.     

Synthesis,Antimicrobial, and Antioxidant Activities of Some Fused Heterocyclic [1,2,4]Triazolo[3,4‐b][1,3,4]thiadiazole Derivatives

In the present work, we synthesized a series of [1,2,4]triazolo[3,4‐b][1,3,4]thiadiazole derivatives ( 6a , 6b , 6c , 6d , 6e , 6f and 7a , 7b , 7c , 7d , 7e , 7f ) by using simple starting materials, namely, β‐amino acids and different aromatic acid hydrazides. The newly synthesized compounds were characterized by mass, IR, ¹H, and¹³C‐NMR spectral data analysis. The newly synthesized compounds were tested for their antimicrobial activities and antioxidant properties. Compound 6c was a potent microbial agent particularly against Staphylococcus aureus (MIC 3.12 µg/mL) and Candida albicans (MIC 6.25 µg/mL) when compared with the reference drugs ciprofloxacin and fluconazole, respectively. The antioxidant activity of the synthesized compounds was also evaluated by 1,1‐diphenyl‐2‐picryl hydrazyl, nitric oxide, and hydrogen peroxide radical scavenging methods. Compounds 6c , 6f , 7c , and 7f showed good radical scavenging activity due to the presence of electron‐donating group on phenyl ring.     

Synthesis and Antimicrobial Activity of Some Novel [4‐(1,2,3‐thiadiazol‐4‐yl)phenoxy]methylene anchored 1,3,4‐triazoles and 1,3,4‐thiadiazoles

A series of novel [4‐(1,2,3‐thiadiazol‐4‐yl)phenoxy]methylene anchored 1,3,4‐triazoles ( 8a , 8b , 8c , 8d , 8e , 8f , 8g , 8h ) and 1,3,4‐thiadiazoles ( 9a , 9b , 9c , 9d , 9e , 9f , 9g , 9h , 9i ) were synthesized from thiosemicarbazide ( 7a , 7b , 7c , 7d , 7e , 7f , 7g , 7h , 7i , 7j ). The structures of these newly synthesized compounds were confirmed on the basis of IR, ¹H‐NMR, mass spectral techniques, and elemental analysis. The in vitro antimicrobial screenings of the synthesized compounds were carried out against four bacterial pathogens, namely Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli, Pseudomonas aeruginosa and three fungal pathogens Candida albicans, Aspergillus niger and Aspergillus clavatus, using broth microdilution minimum inhibitory concentration method. The compounds 7d , 7j , 8a , 9a , 9b , and 9i exhibited promising antibacterial activity against the tested strains, whereas some compounds were found to be active against one of the tested bacterial strains.     

Synthesis of Pyridotriazolopyrimidines as Antitumor Agents

2‐Hydrazino‐5,7‐di‐p‐tolylpyrido[2,3‐d ]pyrimidin‐4(3H )‐one ( 4 ) was prepared and condensed with different aldehydes 5a , 5b , 5c , 5d , 5e , 5f , 5g to give the corresponding hydrazone derivatives 6a , 6b , 6c , 6d , 6e , 6f , 6g . Oxidative cyclization of the latter compounds 6a , 6b , 6c , 6d , 6e , 6f , 6g gave the corresponding pyrido[2,3‐d ][1,2,4]triazolo[4,3‐a ]pyrimidin‐5(1H )‐ones 7a , 7b , 7c , 7d , 7e , 7f , 7g . Furthermore, compound 4 reacted with benzoyl chloride, triethyl orthoformate, acetyl chloride, ethyl chloroformate, and carbon disulphide in alcoholic KOH solution to afford the corresponding pyrido[2,3‐d ][1,2,4]triazolo[4,3‐a ]pyrimidinones ( 7a , 8 , 9 , 10 , 11 ). The reaction of thione 3 or its 2‐methylthio derivative 16 with hydrazonoyl halides 12a , 12b , 12c , 12d , 12e , 12f , 12g , 12h , 12i , 12j , 12k , 12l , 12m yielded the corresponding pyrido[2,3‐d ][1,2,4]triazolo[4,3‐a ]pyrimidinones 15a , 15b , 15c , 15d , 15e , 15f , 15g , 15h , 15i , 15j , 15k , 15l , 15m . The structures of all the products were confirmed by elemental and spectral analyses (¹H NMR, ¹³C NMR, IR, and MS). In addition, the anticancer activity of 20 pyridotriazolopyrimidinones against two cancer cell lines namely MCF‐7 and HepG2 was evaluated, and the results revealed that compounds 7d and 9 have promising activity , compared with doxorubicin, which used as standard reference drug.     

Synthesis,Antiviral, and Antimicrobial Activity of N‐ and S‐Alkylated Phthalazine Derivatives

A series of N‐alkylphthalazinone were synthesized by the reaction of phthalazin‐1(2H)‐one derivatives 1a , 1b , 1c with alkylating agents namely, propargyl, allyl bromide, epichlorohydrin, 1,3‐dichloro‐2‐propanol, 4‐bromobutylacetate, and 1‐(bromomethoxy)ethyl acetate to give the corresponding N‐alkylphthalazinone 2a , 2b , 2c , 3a , 3b , 3c , 5a , 5b , 5c , 6a , 6b , 6c , 7a , 7b , 7c , and 9a , 9b , 9c . Alkylation of phthalazin‐1(2H)‐thione to give a series from S‐alkylphthalazine 12 , 13 , 14 and thioglycosides 15 and 17 was performed. Deprotection of compounds 7a , 7b , 7c , 9a , 9b , 9c , 15 , and 17 resulted in the formation of the corresponding products 8a , 8b , 8c , 10a , 10b , 10c , 16 , and 18 . The structure of newly synthesized compounds was assigned by IR, ¹H, ¹³C NMR, and elemental analysis. Some of these compounds were screened for antiviral and antimicrobial activity.     

Synthesis,Biological Activity of Pyrimidine Linked with Morpholinophenyl Derivatives

A new series of 5‐fluoro‐N⁴‐(3‐(4‐substitutedbenzylamino)phenyl)‐N²‐(4‐morpholinophenyl)pyrimidine‐2,4‐diamine derivatives ( 7a , 7b , 7c , 7d , 7e , 7f , 7g , 7h , 7i , 7j ) are prepared from using an intermediate compound 5‐fluoro‐N⁴‐(3‐(aminophenyl)‐N²‐(4‐morpholinophenyl)pyrimidine‐2,4‐diamine ( 5 ). The structures of the newly synthesized products are established from their spectral ¹H‐NMR, ¹³C‐NMR, ¹⁹F‐NMR, ESI‐MS, and analytical data. Here we report the synthesized compounds and larvicidal activity. All the compounds are screened for their significant larvicidal activity against third instar larvae at 24, 48, and 78‐h time exposure, and values were compared with standard drug Malathion. The Compounds 7i , 7a , 7c , 7f , and 7j exhibited significant activity. However the compounds 7b , 7e , 7d , and 7h showed excellent activity when compared to the above compounds and to standard drug malathion too because of the presence of mild electron withdrawing groups such as trifluoro, fluorine, hydroxy, nitro, and methoxy derivatives which are attached to the benzyl ring.     

硫（醇）代N-对甲苯基/苯基磺酰基氨基羧酸酯类化合物的合成与神经营养活性

根据官能团的组合,设计合成了硫（醇）代N-对甲苯基/苯基磺酰基氨基羧酸酯类化合物,这些化合物的结构¹H NMR, ¹³C NMR, MS 和 HRMS证实,初步的实验结果表明：在10μg/mL浓度下,化合物4a, 4b, 4d, 5c, 5d, 5g, 6b和 6d显示对PC12细胞缺氧损伤具有显著的保护作用,化合物4c, 5b和 6c显示对PC12细胞缺氧损伤具有一定的保护作用;在5μg/mL浓度下,4d和 6d显示对PC12细胞缺氧损伤具有一定的保护作用;初步的实验也表明：在10μg/mL浓度下,4c, 5a, 5c, 5d, 5e和 6b显示对PC12细胞具有一定的促分化作用。     

Synthesis and Antimicrobial Studies of Novel Imidazole Containing Bisazetidinones and Bisthiazolidinone Derivatives

A simple, practical, and efficient approach to new series of imidazole containing bisazetidinones ( 7a , 7b , 7c , 7d , 7e , 7f , 7g , 7h , 7i , 7j and 9a , 9b , 9c , 9d , 9e , 9f , 9g , 9h , 9i , 9j ) was prepared by Staudinger [2 + 2] cycloaddition reaction, and bisthiazolidinones ( 8a , 8b , 8c , 8d , 8e , 8f , 8g , 8h , 8i , 8j and 10a , 10b , 10c , 10d , 10e , 10f , 10g , 10h , 10i , 10j ) were obtained by cyclization of bisimines with thioglycolic acid. The bisimines ( 5a , 5b , 5c , 5d , 5e , 5f , 5g , 5h , 5i , 5j and 6a , 6b , 6c , 6d , 6e , 6f , 6g , 6h , 6i , 6j ) were synthesized by the condensation of 3‐(1‐(3‐aminobenzyl)‐4, 5‐dihydro‐1H‐imidazol‐2‐yl) aniline ( 3 , 4 ) with a series of different substituted aromatic aldehydes. All the newly synthesized target compounds were evaluated for their in vitro antimicrobial activity against two Gram‐positive bacteria and two Gram‐negative bacteria. Additionally, these synthesized compounds were tested for their antifungal activities. Few compounds showed very good antibacterial and antifungal activity.     

Synthesis and Reactions of Some Heterocyclic Candidates Based on 2‐Amino‐4,5,6,7‐tetrahydrobenzo[b]thiophene Moiety as Anti‐Arrhythmic Agents

In continuation of our previous work, a series of novel thiophene derivatives 4 , 5 , 6 , 8 , 9 , 9a , 9b , 9c , 9d , 9e , 10 , 10a , 10b , 10c , 10d , 10e , 11 , 12 , 13 , 14 , 15 , 16 were synthesized by the reaction of ethyl 2‐amino‐4,5,6,7‐tetrahydrobenzo[b]thiophene‐3‐carboxylate ( 1 ) or 2‐amino‐4,5,6,7‐tetrahydrobenzo[b]thiophene‐3‐carbonitrile ( 2 ) with different organic reagents. Fusion of 1 with ethylcyanoacetate or maleic anhydride afforded the corresponding thienooxazinone derivative 4 and N‐thienylmalimide derivative 5 , respectively. Acylation of 1 with chloroacetylchloride afforded the amide 6 , which was cyclized with ammonium thiocyanate to give the corresponding N‐theinylthiazole derivative 8 . On the other hand, reaction of 1 with substituted aroylisothiocyanate derivatives gave the corresponding thiourea derivatives 9a , 9b , 9c , 9d , 9e , which were cyclized by the action of sodium ethoxide to afford the corresponding N‐substituted thiopyrimidine derivatives 10a , 10b , 10c , 10d , 10e . Condensation of 2 with acid anhydrides in refluxing acetic acid afforded the corresponding imide carbonitrile derivatives 11 , 12 , 13 . Similarly, condensation of 1 with the previous acid anhydride yielded the corresponding imide ethyl ester derivatives 14 , 15 , 16 , respectively. The structures of newly synthesized compounds were confirmed by IR, ¹H NMR, ¹³C NMR, MS spectral data, and elemental analysis. The detailed synthesis, spectroscopic data, LD₅₀, and pharmacological activities of the synthesized compounds are reported.     

4‐Toluenesulfonamide as a Building Block for Synthesis of Novel Triazepines,Pyrimidines, and Azoles

N‐{(E)‐(dimethylamino)methylidenearbamothioyl}‐4‐toluenesulfonamide ( 2 ) was obtained by reaction of N‐carbamothioyl‐4‐toluenesulfonamide ( 1 ) with dimethylformamide dimethylacetal or alternatively by the reaction of 1‐(dimethylamino)methylidenethiourea with tosyl chloride. Compound 2 was reacted with substituted anilines to yield anilinomethylidine derivatives 3a , 3b , 3c , 3d , 3e , 3f , 3g . Treatment of 3a , 3b , 3c , 3d , 3e , 3f , 3g with phenacyl bromide gave triazepines 4a , 4b , 4c , 4d , 4e , 4f , 4g and imidazoles 5a , 5b , 5c , 5d , 5e , 5f , 5g . Esterification of compound 3e afforded ester derivative 6 , which was subjected to react with hydrazine to yield hydrazide derivative 7 . Oxadiazole 8 was obtained by reaction of 7 with CS₂/KOH. Compound 3e was treated with o‐aminophenol or o‐aminothiophenol to give benzazoles 9a , 9b . N‐(Diaminomethylidene)‐4‐toluenesulfonamide ( 10 ) reacted with enaminones to yield pyrimidines 11 , 12 , 13 , respectively. The structures of the compounds were elucidated by elemental and spectral analyses. Some selected compounds were screened for their in vitro antifungal activity. In general, the newly synthesized compounds showed good antifungal activity.     

Synthesis and Antimicrobial Activity of 2-Methyl-5-nitroaniline Derivatives:A Structure-Activity Relationship Study

A series of 2‐methyl‐5‐nitroaniline derivatives, 5a – 5k and 6a – 6f , were synthesized in order to determine their in vitro antimicrobial activity. The chemical structures of the synthesized compounds were confirmed by elemental analyses, UV‐visible, FT‐IR, ¹H NMR and ¹³C NMR spectral studies. The structure‐activity relationships of the synthesized compounds were also discussed. Among the synthesized compounds, 5f , 5d , 6b and 6e showed good antimicrobial activity compared to standard drugs.     

A simple one‐pot synthesis of 1,2,3,4‐tetrahydro‐2‐thioxopyrimidine derivatives

5‐Benzoyl‐4‐(substituted phenyl)‐6‐phenyl‐1,2,3,4‐tetrahydro‐2‐thioxopyrimidines ( 4a‐d ) were synthesized using the Biginelli three component cyclocondensation reaction of an appropriate β‐diketone, arylaldehyde, and thiourea in acetic acid under reflux condition in approximately 52‐65% yields. The acetylation of compounds 4a‐d gave 3‐acetyl thioxopyrimidine derivatives 5a‐d . Also, pyrimidothiazine compounds 6a‐d were prepared by a simple one‐pot condensation reaction of starting pyrimidine derivatives 4a‐d and 3‐bromopropionic acid. The structures of compounds were characterized on the basis of elemental analyses, IR, ¹H and ¹³C‐NMR spectra.     

Synthesis and Antimicrobial Activity of Some New N‐substituted‐5‐arylidene‐thiazolidine‐2,4‐diones

A total of 17 new N‐substituted derivatives ( 2b , 2c , 2d , 2e , 2f , 2g , 2h , 2i , 2j , 2k and 3b , 3c , 3d , 3e , 3f , 3g , 3h ) of 5‐((2‐phenylthiazol‐4‐yl)methylene) thiazolidine‐2,4‐dione ( 2a ) and 5‐(2,6‐dichloro‐ benzylidene)thiazolidine‐2,4‐dione ( 3a ) were synthesized. The structural elucidation of the newly synthesized compounds was based on elemental analysis and spectroscopic data (MS, ¹H NMR, ¹³C NMR), and their antimicrobial activities were assessed in vitro against several strains of Gram‐positive and Gram‐negative bacteria and one fungal strain (Candida albicans) as growth inhibition diameter. Some of them showed modest to good antibacterial activity against Gram‐negative Escherichia coli and Salmonella typhimurium and Gram‐positive Staphylococcus aureus, Bacillus cereus, and Enterococcus fecalis bacterial strains, whereas almost all the compounds were inactive against Listeria monocytogenes. All of the synthesized compounds showed moderate to very good activity against C. albicans.     

Synthesis and Antimicrobial Activity of Some Novel Substituted Bis‐Pyridone,Pyrazole, and Thiazole Derivatives

A variety of novel bis‐heterocyclic derivatives were synthesized via the reaction of bis‐cyanoacetanilide derivative 3 with various aromatic aldehydes (1:2 molar ratio), to give the corresponding bis‐arylidene derivatives 5a , 5b , 5c , 5d , 5e , 5f , 5g , 5h , 5i , 5j , 5k , 5l , 5m . On the other hand, reacting compound 3 with substituted 2‐hydroxybenzaldehydes 6a , 6b , 6c afforded 2‐iminochromene‐3‐carboxamides 7a , 7b , 7c . The reaction of compound 5 with malononitrile afforded the novel bis‐pyridones 9a , 9b , 9c , 9f , 9g , 9h . The reaction of 5 with hydrazine derivatives afforded pyrazoles 11a , 11b , 11c , 11d , 11e , 11f , respectively. Compound 3 reacts with phenyl isothiocyanate in the presence of potassium hydroxide at room temperature followed by addition of some different halo‐carbonyl compounds to afford bis‐poly‐functionalized thiazole derivatives 13a , 13b , 13c . The bis‐enamine derivative 15 reacts also with hydrazine hydrate, guanidine, and hydroxylamine to give bis‐pyrazole 17 , pyrimidine 19 , and isoxazole 21 derivatives, respectively. Some of the newly synthesized compounds show moderate to high antimicrobial activity.     

Four component one‐pot synthesis of novel 7,8‐dihydroquinolin‐5(1H,4H,6H)‐one derivatives containing an ionone unit and in vitro antioxidant activity

A new class of novel 7,8‐dihydroquinolin‐5‐(1H,4H,6H)‐one derivatives ( 5a , 5b , 5c , 5d , 5e , 5f , 5g , 5h , 5i , 5j , 5k ) were synthesized by the one‐pot four‐component condensation of dimedon, α‐ionone, ammonium acetate, and benzaldehyde derivatives. The structures were characterized by elemental analysis, IR, ¹H‐NMR, and ¹³C NMR spectral studies. All the title compounds were screened for antioxidant properties and some of them found to exhibit potent in vitro antioxidant activity. J. Heterocyclic Chem., (2011).     

A “One Pot,” Environmentally Friendly,Multicomponent Synthesis of 2‐Amino‐5‐cyano‐4‐[(2‐aryl)‐1H‐indol‐3‐yl]‐6‐hydroxypyrimidines and Their Antimicrobial Activity

A series of multifunctional 2‐amino‐5‐cyano‐4‐[(2‐aryl)‐1H‐indol‐3‐yl]‐6‐hydroxypyrimidines ( 4a , 4b , 4c , 4d , 4e , 4f ) was synthesized by multicomponent reaction of 3‐formylindole ( 1 ), cyanoethylacetate ( 2 ), and guanidine hydrochloride ( 3 ) with NaOH by using green chemical techniques, viz. microwave irradiation and grindstone technology. The same reactants when refluxed in ethanol also gave titled compounds ( 4a , 4b , 4c , 4d , 4e , 4f ). Compared with conventional procedure, the reaction can be carried out under milder conditions, requiring a shorter reaction time and giving higher yields following the green chemistry methodology. All the synthesized compounds have been characterized on the basis of elemental analyses and spectral data (IR, ¹H NMR, ¹³C NMR, and mass). All synthesized compounds were also evaluated for their antimicrobial activity against nine pathogenic bacteria, antifungal activity against Rhizopus stolonifer, Aspergillus flavus, and Fusarium oxysporum and antibacterial activity against Escherichia coli and Pseudomonas aeruginosa at different concentrations. Most of the compounds showed mild to moderate activity.     

Utility of the Pfitzinger Reaction in the Synthesis of Novel Quinoline Derivatives and Related Heterocycles

2‐(2‐Amino‐3,5‐dinitrophenyl)‐2‐oxoacetic acid ( 2 ) was obtained from hydrolysis of 5,7‐dinitroisatin ( 1 ) in alkaline media. A novel quinoxaline derivative ( 3 ) was synthesized from the reaction of the same compound ( 1 ) with o‐phenylenediamine. Reacting 2 with ethyl 3‐oxo‐3‐phenylpropanoate yields 6,8‐dinitro‐2‐phenylquinoline‐3,4‐dicarboxylic acid ( 4 ). Then, 4 was converted into new quinoline‐diacylchloride, quinoline‐ester, quinoline‐dicarboxamide, pyridazine, and pyrroledione derivatives ( 5 , 6a , 6b , 6c , 6d , 7a , 7b , 7c , 7d , 8 , 9 , 10a , 10b , 10c , 10d , 11a , 11b , 12 ) with SOCl₂, alcohols, amines, and hydrazines, respectively. The structures of synthesized compounds were clarified by ¹H NMR, ¹³C NMR, IR, mass and elemental analysis methods.