5-(5-Aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate and new cyclic C-glycoside analogues from carbohydrate precursors with MAO-B, antimicrobial and antifungal activities

Cyclization of acyclic C-glycoside derivatives 1a,b to 2a,b as the major isomers, and 4a,b as the minor isomers were carried out. The isopropylidene derivatives 3a,b were prepared, as well as the hydrazide derivative 6, which was condensed with a variety of aldehydes to give hydrazones 7a-e which were also prepared from the compounds 12a-e. Acetylation of 7a,d gave the corresponding acetyl derivatives 8a,d, respectively. In addition, the dicarbonyl compound 9 was prepared in the hydrate form, which reacted with a number of aroylhydrazines to give the corresponding bisaroylhydrazones 10a-d, which were cyclized into 1,3,4-oxadiazoles 11a-d. Furthermore, two of the prepared compounds were examined to show the ability to activate MAO-B. In addition a number of prepared compounds showed antibacterial and antiviral activities.     

S-, S,S-, S,S,S- Und N,S-Substituierte Dienverbindungen Und Dibutadienylpiperazinverbindungen Von 2-Nitropentachlorbutadien

Nitrodiene compound 1 was stirred with allylthiol for a long time and compound 3 was obtained. Compound 1 gave bis(thio)substituted 2-nitrodiene compound 4 and tris(thio)substituted 2-nitrodiene compound 5 with 2 moles allylthiol in the presence of NaOH in ethanol. Mono(allylthio)substituted diene compound 3 gave dibutadienyl substituted piperazine compounds with piperazine 6 in CH 2 Cl 2 (or diethylether). Compound 3 gave compound 9 with compound 8 . Compounds 11a-e have been obtained from the reaction of compound 3 with compounds 10a-e . Nach langem Rühren von der Verbindung 1 mit Allylthiol entsteht die Verbindung 3 . Die Verbindung 1 liefert mit zwei Mol von Allylthiol in ethanolischer Natronlunge die bis(thio)substituierte 2-Nitrodienverbindung 4 und tris(thio)substituierte Dienverbindung 5 . Mono(allylthio)substituierte Dienverbindung 3 ergibt mit Piperazine in CH 2 Cl 2 (oder in Ether) die dibutadienylsubstituierte Piperazinverbindung 7 . Die Verbindung 3 liefert mit der Verbindung 8 die Verbindung 9 . Durch die Reaktion von der Verbindungen 10a-c wurden die Verbindungen 11a-e erhalten.     

Functionalized 2‐Hydrazinobenzothiazole with Isatin and Some Carbohydrates under Conventional and Ultrasound Methods and Their Biological Activities

Several chemical reactions were carried out on 3‐(benzothiazol‐2‐yl‐hydrazono)‐1,3‐dihydro‐indol‐2‐one ( 2 ). 3‐(Benzothiazol‐2‐yl‐hydrazono)‐1‐alkyl‐1,3‐dihydro‐indol‐2‐one 3a , 3b , 3c have been achieved. Reaction of compound 2 with ethyl bromoacetate in the presence of K₂CO₃ resulted the uncyclized product 4 . Reaction of compound 2 with benzoyl chloride afforded dibenzoyl derivative 5 . Compound 2 was smoothly acetylated by acetic anhydride in pyridine to give diacetyl derivative 6b . Moreover, when compound 4 reacted with methyl hydrazine, it yielded dihydrazide derivative 7 , whereas the hydrazinolysis of this compound with hydrazine hydrate gave the monohydrazide derivative 8 . {N‐(Benzothiazol‐2‐yl‐N′‐(3‐oxo‐3,4‐dihydro‐2H‐1,2,4‐triaza‐fluoren‐9‐ylidene)hydrazino]‐acetic acid ethyl ester ( 9 ) was prepared by ring closure of compound 8 by the action of glacial acetic acid. In addition, the reaction of 2‐hydrazinobenzothiazole ( 1 ) with d ‐glucose and d ‐arabinose in the presence of acetic acid yielded the hydrazones 10a , 10b , respectively. Acetylation of compound 10b gave compound 11b . On the other hand, compound 13 was obtained by the reaction of compound 1 with gama‐d ‐galactolactone ( 12 ). Acetylation of compound 13 with acetic anhydride in pyridin gave the corresponding N¹‐acetyl‐N²‐(benzothiazolyl)‐2‐yl)‐2,3,4,5,6‐penta‐O‐acetyl‐d ‐galacto‐hydrazide ( 14 ). Better yields and shorter reaction times were achieved using ultrasound irradiation. The structural investigation of the new compounds is based on chemical and spectroscopic evidence. Some selected derivatives were studied for their antimicrobial and antiviral activities.     

Synthesis of Some New Pyrazolopyridines,Pyrazolothienopyridines, Pyrazolopyridothienopyrimidines and Pyrazolopyridothienotriazines

Pyrazolo[3,4-b]pyridine derivative 3a was prepared and reacted with methyl iodide to give 4 or 5 depending on reaction conditions. Oxidation of 3a with iodine produced the corresponding disulphide derivative 6 , whereas oxidation with KMnO 4 gave the corresponding oxo derivative 7 . Oxidation of 4 afforded the corresponding sulphone derivative 8 , which on boiling in NaOH solution gave 7 . The reaction of compound 3a with chloroacetonitrile, ethyl chloroacetate, phenacyl bromide, and chloroacetanilide afforded 9a , b , 11 , and 12 respectively. Cyclication of the products 9a , b , 11 , and 12 yielded 10a , b , 13 , and 14 respectively. The reaction of compound 14 with ethyl orthoformate, nitrous acid, acetic anhydride, benzaldehyde, urea, CS 2 , and phenyl isothiocyanate afforded compounds 15-21 respectively.     

New N6‐substituted 8‐alkyl‐2‐phenylmethylsulfanyl‐adenines. II

Title compounds bearing substituents on C(2), C(6) and C(8) were prepared from a newly synthesized pyrimidine derivative 11. The new pyrimidine 11 was generated from compound 2 through two different synthetic schemes. In one pathway, compound 2 was nitrosated, reduced and alkylated to produce com pounds 9 , 10 and 11 respectively (Scheme). In an alternate route using compound 2 as the starting material, a coupling reaction using the diazonium salt derived from p‐methylaniline afforded the azo derivative 7 , which was subsequently alkylated and reductively cleaved to form compounds 8 and 11 respectively (See Scheme). Compound 11 was annulated to the corresponding hypoxanthine derivatives 12–14 ; compounds 12 and 13 were chlorinated with phosphorus oxychloride, then reacted with amines to yield compound 17 and 20 respectively. Compounds 21 , 22 and 23 were obtained by oxidation of the corresponding sulfide as depicted in Scheme. Alkylation of the thiol function of 1 gave a mixture of 3 and 4. Compound 3 was chlo rinated to 5. Nitration of 5 resulted in electrophilic aromatic substitution of the aryl ring and concomitant oxidation of the sulfide to the sulfoxide, producing 6.     

Design,Synthesis of Novel Thiourea and Pyrimidine Derivatives as Potential Antitumor Agents

1,3‐Bis‐(arylidene)thiourea derivatives ( 11a‐c ) were prepared by reacting thiourea ( 9 ) with bezaldehyde, p‐chlorobenzaldehyde or p‐anisaldehyde ( 10a‐c ) respectively. Further reaction of ( 11b ) with acetyl acetone, ethyl acetoacetate, malononitrile and acetic anhydride gave tetrahydropyrimidine‐2‐thiones ( 12‐14 ) and 1,3‐diacetyl thiourea ( 15 ). Compound ( 11b ) reacted with chloroacetyl chloride to give the corresponding pyrimidin‐4‐one derivative ( 16 ). Reaction of ( 12‐14 ) with acetic acid in aqueous sodium nitrite yielded the corresponding oxime derivatives ( 17‐19 ). The triazole ( 20 ) was achieved via refluxing of ( 19 ) in dimethylformamide. Reaction of ( 16 ) with mercaptoacetyl chloride gave the sulfanyl‐acetic acid ( 21 ) which afforded the dihydrazinyl ( 22 ) up on treatment with hydrazine hydrate. Newly synthesized compounds ware characterized by elemental analyses and spectral data (IR, ¹H‐NMR, ¹³C‐NMR and mass spectra). The investigated compounds were screened for their cytotoxicity, i.e. compounds 19 , 20 and 22 exhibited highly potential antitumor activity.     

Application of Phase Transfer Catalysis in Heterocyclic Synthesis: Synthesis of Some New Polyfunctional Thiophenes,Thiopyrans, Pyridines and Oxazines

The reaction of compound 1 with CS 2 and different active halo compounds gave the corresponding thiophene derivatives 2a,b-4a,b , whereas treatment of compound 1 with CS 2 and active methylene compounds afforded the corresponding thiopyran derivatives 5a,b , 6a,b , 7 , and 8 . Also, 1,3-thioxane derivatives 9 and 10 were obtained by reacting compound 1 with CS 2 and different cycloalkanones. Thiophene and pyrrolidene derivatives 11 , 12a,b , and 13a,b were obtained by reacting compound 1 with phenyl isothiocyanate and different halo compounds. The active methylene compounds and/or cycloalkanones were treated with compound 1 in the presence of phenyl isothiocyanate to give pyridines, thiopyran and oxazine derivatives 14a,b-16a,b , 17a-19a , and 19b , respectively.     

Part 1: Synthesis of Polyfused Heterocyclic Systems Derived From 3-Phenyl-5,6,7,8-tetrahydro[1,2,4]triazolo[3,4- b ][1,3,4]thiadiazepine-6,8-dione

3-Phenyl-5,6,7,8-tetrahydro[1,2,4]triazolo[3,4- b ][1,3,4]thiadiazepine-6,8-dione ( 1 ) was condensed with o -aminothiophenol, 2-amino-ethanol or cystamine to afford compounds 2-4 respectively. Treatment of compound 1 with dimethylthiomethylenemalononitrile yielded the corresponding pyrano[3,2- f ][1,2,4]triazolo[3,4- b ]-[1,3,4]thiadiazepine derivative 5 . 7-[5-Amino-1,3-dithiolan-2-ylidene]-3-phenyl-5,6,7,8-tetrahydro[1,2,4]triazolo[3,4- b ][1,3,4]thiadiazepine-6,8-dione ( 6 ) was obtained by treating compound 1 with CS 2 and chloroacetonitrile. Thiation of compound 1 gave the corresponding thioanalog 7 , which in turn was condensed with malononitrile to give 3-phenyl-5,6,7,8-tetrahydro[1,2,4]triazolo[3,4- b ][1,3,4]thiadiazepine-6-one-8-ylidenemalononitrile ( 8 ). On treating compound 8 with benzaldehyde or p -nitrobenzaldehyde, pyrano[1,2,4]triazolo[1,3,4]thiadiazepin derivatives 9a , b , respectively, were obtained. Compound 8 was treated with CS 2 and methyl iodid to give the corresponding dithiomethylmethylene derivative 10 which was subjected to react with aniline to give pyrido[1,2,4]triazolo[1,3,4]thiadiazepine derivative 11 . Compound 8 was treated with 3-aminopyridine, o -aminothiophenol, or o -phenylenediamene to yield compounds 12 and 13a , b respectively. Finally, tertiary amines or activated phenols were condensed with compound 8 to yield compounds 14 and 15a , b respectively.     

Synthesis of Some New [1,8]Naphthyridine,Pyrido[2,3‐d]‐Pyrimidine,and Other Annulated Pyridine Derivatives

2‐Aminopyridine‐3‐carbonitrile derivative 1 reacted with each of malononitrile, ethyl cyanacetate, benzylidenemalononitrile, diethyl malonate, and ethyl acetoacetate to give the corresponding [1,8]naphthyridine derivatives 3 , 5 , 8 , 11 , and 14 , respectively. Further annulations of 3 , 5 , and 8 gave the corresponding pyrido[2,3‐b][1,8]naphthyridine‐3‐carbonitrile derivative 17 , pyrido[2,3‐h][1,6]naphthyridine‐3‐carbonitrile derivatives 18 and 19 , respectively. The reaction of 1 with formic acid, formamide, acetic anhydride, urea or thiourea, and 4‐isothiocyanatobenzenesulfonamide gave the pyridopyrimidine derivatives 20a , b , 21 , 22a , b , and 26 , respectively. Treatment of compound 1 with sulfuric acid afforded the amide derivative 27 . Compound 27 reacted with 4‐chlorobenzaldehyde and 1H‐indene‐1,3(2H)‐dione to give the pyridopyrimidine derivative 28 and spiro derivative 30 , respectively. In addition, compound 1 reacted with halo compounds afforded the pyrrolopyridine derivatives 32 and 34 . Finally, treatment of 1 with hydrazine hydrate gave the pyrazolopyridine derivative 35 . The structures of the newly synthesized compounds were established by elemental and spectral data.     

An Approach to Polysubstituted Triazipines,Thiadiazoles and Thiazoles Based on Benzopyran Moiety Through The Utility of Versatile Hydrazonoyl Halides as In Vitro Monoamine Oxidase Inhibitors

The chromene compound 1 is used as a key intermediate for synthesis of new heterocyclic compounds, and it reacted with hydrazonoyl chlorides in presence of TEA to give the amidrazone derivatives 3a , 3b , 3c , 3d , 3e , 3f , 3g , 3h , which were cyclized to the corresponding triazepines 5a , 5b , 5c , 5d , 5e , 5f , 5g , 5h on boiling with sodium ethoxide. Conversion of compound 1 to the methylthiocarbamate derivative 6 was performed through its reaction with carbon disulfide and KOH followed by treatment with methyl iodide. Compound 6 reacted with hydrazonoyl chlorides in presence of TEA to give thiadiazoles 8a , 8b , 8c , 8d , 8e , 8f , 8g . In addition, chromene 1 combined with aminodithiocarbamic acid in DMF under reflux to furnish the thiosemicarbazide derivative 9 , which in turn interacted with several hydrazonoyl chlorides to give the thiazole derivatives 11a , 11b , 11c , 11d , 11e . The structures of the prepared compounds were confirmed from their spectroscopic data and elemental analysis. The synthesized compounds were tested against both monoamine oxidase (MAO)‐A and MAO‐B and corrected to analyses showed good inhibitory activities especially against MAO‐A.     

Neue Thiosubstituierte Butadien- Und Butenin Verbindungen Aus Hexachlorbutenen Und Thiolen

2,3-Di-H-butene compound 1 gave compounds 3a-f , 4a , 4e , and 5a-d in the presence of thiols 2a-f and Et 3 N (or NaOH). Compound 7e was obtained from the reaction of 1,3-Di-H-butene 6 with naphthylthiol in DMF. In the presence of NaOH, compound 6 and 2 mmol of thiol 2g in EtOH gave compounds 8 , 9 , 10 , and 11 .     

四氟乙烯齐聚体的反应 四氟乙烯四、五聚体和芳香胺的反应

前已报道四氟乙烯四聚体(全氟-3,4-甲基己烯-3)(1)、五聚体(全氟-3,4-二甲基-4-乙基己烯-2)(2)和脂肪烷氧以及脂肪胺的亲核反应.本文报道化合物1,2和芳香胺如苯胺、β-萘胺的反应.由于烯烃1、2双键处于分子中间,因而当亲核试剂进攻时,双键容易发生重排,生成的末端基烯烃更具反应性,故导致一取代、二取代、三取代以及环化降解等复杂产物.     

Synthesis and Reactions of Some Novel Nicotinonitrile,Thiazolotriazole, and Imidazolotriazole Derivatives for Antioxidant Evaluation

The novel 2-(1H)-pyridone, the lead compound of the pyridone derivative 1, reacted with an electrophilic reagent (ethyl chloroacetate) to give the corresponding ester 2. Condensation of compound 2 with thiosemicarbazide and/or hydrazine hydrate afforded the mercaptotriazole and the corresponding acetic acid hydrazide derivatives 3 and 4, respectively. The latter compound reacted with ethyl acetoacetate, ethyl cyanoacetate, and maleic anhydride to give compounds 5, 6, and 7, respectively. Alkylation of compound 3 with methyl iodide or chloroacetic acid afforded methylsulfanyltriazole and thiazolotriazole derivatives 8 and 9, respectively. Compound 8 reacted with glycine to afford the imidazotriazole derivative 10. Both compounds 9 and 10 reacted with glucose and benzaldehyde to give compounds 11, 12, 13, and 14, respectively. Some of the prepared products were selected and subjected to screening for their antioxidant activity.     

N,S-Substituted Dienes from Mono(arylthio)substituted- and S-, S,S-Substituted Dienes

Mono(thio)substituted dienes 1a-1b gave compounds 3a-c and 5d-g with piperazine and piperidine derivatives in dichloromethane. Compounds 8 , 9 , and 10 were obtained from the reactions of perchlorobutadiene ( 6 ) with 1,4-butanedithiol ( 7 ) in ethanol in the presence of sodium hydroxide. Compounds 12a-b , 13a-b were obtained from the reactions of perchlorobutadiene ( 6 ) with allylmercaptan (CH 2 =CH--CH 2 --SH) and mercaptoethanol (HO--CH 2 --CH 2 --SH).     

Synthese von Trifluoromethyl-substituierten Schwefel-Heterocyclen unter Verwendung von 3,3,3-Trifluorobrenztraubensäure-Derivaten

Synthesis of Trifluoromethyl-Substituted Sulfur Heterocycles Using 3,3,3-Trifluoropyruvic-Acid Derivatives The reaction of methyl 3,3,3-trifluoropyruvate ( 1 ) with 2,5-dihydro-1,3,4-thiadiazoles 4a, b in benzene at 45° yielded the corresponding methyl 5-(trifluoromethyl)-1,3-oxathiolane-5-carboxylates 5a, b (Scheme 1) via a regioselective 1,3-dipolar cycloaddition of an intermediate ‘thiocarbonyl ylide’ of type 3 . With methyl pyruvate, 4a reacted similarly to give 6 in good yield. Methyl 2-diazo-3,3,3-trifluoropropanoate ( 2 ) and thiobenzophenone ( 7a ) in toluene underwent a reaction at 50°; the only product detected in the reaction mixture was thiirane 8a (Scheme 2). With the less reactive thiocarbonyl compounds 9H-xanthene-9-thione ( 7b ) and 9H-thioxanthene-9-thione ( 7c ) as well as with 1,3-thiazole-5(4H)-thione 12 , diazo compound 2 reacted only in the presence of catalytic amounts of Rh₂(OAc)₄. In the cases of 7a and 7b , thiiranes 8b and 8c , respectively, were the sole products (Scheme 3). The crystal struture of 8c has been established by X-ray crystallography (Fig.). In the reaction with 12 , desulfurization of the primarily formed thiirane 14 gave the methyl 3,3,3-trifluoro-2-(4,5-dihydro-1,3-thiazol-5-ylidene)propanoates (E)-and (Z)- 15 (Scheme 4). A mechanism of the Rh-catalyzed reaction via a carbene addition to the thiocarbonyl S-atom is proposed in Scheme 5.     

Novel polycyclic heterocycles. X. Synthesis of 3-amino derivatives derived from 1,2-dihydro-l 1 (trifluoromethyl)-3H,7H-quino [8,1-cd][ 1,5]benzoxazepin-3-one

The reactions of the tetracyclic ketone, 1,2-dihydro-11-(trifluoromethyl)-3H,7H-quino[8,1-cd] [1,5]benzoxazepin-3-one ( 1 ) with pyrrolidine, piperazine, N-methylpiperazine, and dimethyl-amine gave the enamines 2, 13, 11 , and 4 . These were reduced with sodium borohydride to the corresponding 3-amino derivatives 3, 14, 12 , and 5 . The 3-(2-hydroxyethylpiperazino) derivative ( 8 ) was obtained from the 3-chloro compound ( 7 ); 7 was prepared from the carbinol ( 6 ). The 3-NH₂ derivative ( 10 ) was obtained by reduction of the oxime ( 9 ). In 3, 5, 6, 7, 8, 10, 12 , and 14 , the -OCH₂ protons were non-equivalent, since in the pmr spectrum of each of these compounds there was seen a symmetrical, perturbed AB quartet, with a common JAB of 12 cps, that must be attributed to geminal interproton coupling. This phenomenon had not previously been observed with 1, 9 , or the enamines, since in their pmr spectra, the -OCH₂ protons had invariably been seen as singlets.     

Syntheses of substituted-oxazolo-1,3,4-thiadiazoles, 1,3,4-oxadiazoles,and 1,2,4-triazoles

Starting from readily available methyl 5-methyloxazole-4-carboxylate ( 1 ) and 4-methyl-5-oxazolylcar-boxylic acid hydrazide ( 11 ) the title compounds were prepared. The reaction of compound 1 with hydrazine hydrate afforded the corresponding hydrazide 2 . The reaction of compound 2 with formic acid yielded 1-formyl-2-(5-methyloxazole-4-carboxyl)hydrazine ( 3 ). Refluxing of the latter with phosphorus pentasulfide in xylene gave compound 5 in 62% yield. The reaction of compound 3 with phosphorus pentoxide afforded compound 4 . Starting from hydrazide 11 , compounds 13 and 14 were prepared similarly. Reaction of compound 2 with substituted isothiocyanate yielded compound 9 which was cyclized in basic medium to 4-alkyl-5-(5-methyl-4-oxazolyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione ( 10 ). The isomer 19 was prepared similarly. Methylation and subsequent oxidation of compound 19 gave compound 21 . Reaction of the acid 7 with thiosemicarbazide in the presence of phosphorus oxychloride gave 2-amino-5-(5-methyl-4-oxazolyl)1,3,4-thiadiazole ( 8 ). 2-Amino-5-(4-methyl-5-oxazolyl)-1,3,4-thiadiazole ( 17 ) was prepared from acyl chloride 15 by the usual method.     

Synthesis of new visnagen and khellin furochromone pyrimidine derivatives and their anti-inflammatory and analgesic activity

6-[(4-Methoxy/4,9-dimethoxy)-7-methylfurochromen-5-ylideneamino]-2-thioxo-2,3-dihydropyrimidin-4-ones 1a,b were prepared by reaction of 6-amino-2-thiouracil with visnagen or khellin, respectively. Reaction of 1a,b with methyl iodide afforded furochromenylideneaminomethylsulfanylpyrimidin-4-ones 2a,b. Compounds 2a,b were reacted with secondary aliphatic amines to give the corresponding furochromen-ylideneamino-2-substituted pyrimidin-4-ones 3a-d. Reaction of 3a-d with phosphorus oxychloride yielded 6-chlorofurochromenylidenepyrimidinamines 4a-d, which were reacted with secondary amines to afford furochromenylideneamino-2,6-disubstituted pyrimidin-4-ones 5a-d. In addition, reaction of 5a-d with 3-chloropentane-2,4-dione gave 3-chloro-furochromenylpyrimidopyrimidines 6a-d. The latter were reacted with piperazine and morpholine to give 1-(furochromenyl)-pyrimidopyrimidine-3,6,8-triylpiperazines or -3,6,8-triylmorpholines 7a-d. The chemical structures of the newly synthesized compound ware characterized by IR, 1H-NMR, 13C-NMR and mass spectral analysis. These compounds were also screened for their analgesic and anti-inflammatory activities. Some of them, particularly 3-7, exhibited promising activities.     

Pyrimidine derivatives and related compounds. 38. Synthesis of 1,3-oxazine-2,4-diones and their reaction with nucleophiles. Ring transformation of 1,3-oxazines to pyrimidines

5,6-Unsubstituted 1,3-oxazine-2,4-diones ( 3 ) and 6-unsubstituted 5-methyl-1,3-oxazine-2,4-diones ( 4 ) were prepared by reduction of the corresponding 6-chloro derivatives ( 1 and 2 ). Treatment of 6-chloro-3-methyl-1,3-oxazine-2,4-dione ( 1a ) with sodium azide, sodium cyanide, secondary amines and aniline gave the corresponding 6-substituted compounds ( 7, 9, 10 and 11 ) while the reaction of 1a and 2a,b with primary aliphatic amines such as methylamine and ethylamine caused a ring transformation to pyrimidine ring system giving barbituric acids ( 13a-d ).     

Studies on organophosphorus compounds: Synthesis and reactions of [1,2,4,3]triaza‐phospholo[4,5‐a]quinoxaline derivative

2,4‐Bis‐(4‐methoxyphenyl)‐1,3,2,4‐dithiadiphosphetane‐2,4‐disulfide (Lawesson's reagent) ( 1 ) reacted with 2‐hydrazino‐3‐methyl‐quinoxaline ( 2 ) to give [1,2,4,3]‐triazaphospholo[4,5‐a]quinoxaline derivative 3 . The Mannich reaction using different amines on compound 3 gave Mannich bases 4a–d . Also, compound 3 reacted with formaldehyde to give the corresponding 2‐hydroxymethyl derivative 5 , which upon reaction with thionyl chloride gave the corresponding chloromethyl derivative 6 . Treatment of compound 6 with some thiols yielded the corresponding sulfides 7a–d . Acylation of compound 3 gave acylated compounds 8a,b . Compound 9 , which was prepared through the reaction of compound 3 with ethyl cyanoacetate, was investigated as a starting material for the synthesis of some new heterocyclic systems 10–13 . Also, reaction of compound 9 with carbon disulfide and 2 equivalents of methyl iodide in a one‐pot reaction yielded the corresponding ketene‐S,S‐acetal 14 , which in turn reacted with bidentates to give some new heterocycles 15–17 . © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:520–529, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20473