E. M. Kandeel

One-Pot Three-Component Synthesis of β -Acylaminoketones Containing a Thiophene Ring by the Use of Tetrachlorosilane-Zinc Chloride as a Binary Reagent Under Ambient Conditions

A new route for the synthesis of β -acylaminoketones containing a thiophene ring through multicomponent condensation reaction of different ketones, different aldehydes, and different nitriles with tetrachlorosilane (TCS) and zinc chloride as the binary reagent is described.

A NOVEL ROUTE FOR THE DIRECT SYNTHESIS OF SECONDARY AMIDES FROM ALDEHYDES

Abstract We describe a unique, general redox process for the preparation of secondary amides by the interaction of aldehydes and nitriles in the presence of two equivalents of iodotrichlorosilane (ITCS).

Tetrachlorosilane-Zinc Chloride as a New Potent Binary Reagent for One-Pot, Three-Component Synthesis of Mannich-Type Products

A combination of tetrachlorosilane and zinc chloride in dichloromethane as an efficient and ambient binary reagent to promote a one-pot amidoalkylation reaction of enolizable ketones, aromatic aldehydes with acetonitriles, or benzonitrile have been developed. The newly synthesized β-acetamidoketones 3 and β-benzamidoketones 5 were obtained in good yields.

SYNTHESIS OF PYRROLO-, THIENOPYRROLO-, BENZOTHIENOPYRROLOQUINOLINES AS WELL AS TRIAZOLOINDOLE DERIVATIVES

Abstract Substituted pyrroloquinoline, thienopyrroloquinoline, benzothieno-pyrroloquinoline and triazoloindole derivatives have been synthesized starting from 6-amino-2,3-diphenylindole. The structures of the newly synthesized compounds and MS data.

The Direct Synthesis of Secondary Amides from Aldehydes; A Novel General Redox Procedure Mediated by Iodotrichlorosilane (ITCS)

Abstract A unique, general redox process for the preparation of secondary amides by the interaction, of aldehydes with nitriles in the presence of two equivalents of iodotrichlorosilane (ITCS) is described and possible pathways are discussed.

Synthesis of Some New Naphthopyran, Pyrazole, Pyridine, and Thienobenzochromene Derivatives Using 1-(1-Hydroxy-2-naphthyl) Ethanone as a Versatile Starting Material

Treatment of the enaminone 2 , prepared from 1-(1-hydroxy-2-naphthyl)ethanone 1 and N,N-dimethylformamide dimethylacetal with acetic acid, thionyl chloride, or bromine, gave the corresponding 4-oxo-4H-naphtho[1,2-b]pyran derivatives 3, 4, and 5 . Refluxing of p-toluidine or p-anisidine with 2 afforded compounds 6 and 7 , respectively. The naphtho[1,2-b]pyran-3-carbaldehyde 9 was prepared via the acetylation of 2 . Condensation of 9 with malononitrile or ethyl cyanoacetate gave the pyridine derivatives 10 and 11 . Refluxing of 9 with hydrazine hydrate, phenylhydrazine, semicarbazide hydrochloride, or thiosemicarbazide afforded the pyrazole derivatives 12, 13, 14 , and 15 respectively. Reaction of ethanone 1 with malononitrile gave the chromene carbonitrile derivative 16 . Treatment of 16 with malononitrile afforded the chromene malononitrile derivative 17 . Also, compound 17 was obtained from the reaction of 1 with excess of malononitrile and catalytic piperidine. Treatment of 16 with ethyl cyanoacetate produced compound 18 . When 16 was treated with elemental sulfur, theino[3,4-c]benzochromene derivative 19 was produced. Hydrolysis of 16 with hydrochloric acid yielded the benzochromene carbonitrile derivative 20 which on heating with elemental sulfur afforded the theinobenzochromene derivative 21 . Treatment of 21 with acetic anhydride, p-chlorobenzaldehyde, phenyl isothiocyanate, or thionylchloride furnished compounds 22, 23, 24 , and 25 , respectively.

Reactions with Cyclic Amidenes III: Synthesis of Some New Fused Pyrazole Derivatives

Abstract Diazotised 5-amino-3-hydroxy-4-phenylazopyrazole (1 a) and 3,5-diamino-4-phenylazo-pyrazole(1 b) coupled with active methylene reagents to yield the pyrazolo[1,5-c]-as-triazine derivatives (3a, b-5 a, b). On the other hand coupling of diazotised 1 a, with β-naphthal has afforded the acyclic azo derivative(6). Whereas diazotised 1 a underwent intramolecular cyclisation into the pyrazolo[1,5-c]-1,2,3,4-tetrazine derivative (3)on attemptet addition to acrylonitrile, diazotised 1 b reacted with acrylonitrile under the same conditions to yield the pyrazolo[1,5-c]-pyridazine derivative (4). Compounds 1 a, b reacted with benzoylisothiocyanate to yield the pyrazol-5-ylthiourea derivatives (10 a, b). Where as 10 a readily cyclised into the pyrazolo[3,4-c]-as-triazine derivative (11) on refluxing with pyridine, compound 10 b hydrolysed under the same conditions into the pyrazol-5-ylthiourea derivative (12).

Studies on 3,5-Diamino Pyrazoles: Chemical Behavior of 4-Phenylazo-3,5-diaminopyrazoles

The behaviour of 3,5-diamino-4-phenylazopyrazole (1) toward isothiocyanates, acrylonitrile and ethyl ethoxymethylenecyanoacetate is investigated. An improved synthesis of 4-unsubstituted-3,5-diaminopyrazoles by an arylazo removal reaction is also reported.

Pyrimidine Derivatives and Related Compounds, VII Synthesis of Some New Pyrazolo [1,5-a] -S-triazines, Pyrazolo [3,4-c] -as-triazines, Pyrazolo [1,5-a] pyrimidines and Pyrazolo [3,4-b] pyrones

3-Amino-4-phenylhydrazono-2-pyrazolin-5-one (1) reacts with isothiocyanate to yield the corresponding pyrazolylthiourea derivatives (2 a-c). Whereas 2 a reacted with hydrazines to yield the pyrazolylamino-1,2,4-triazoles (3 a, b), it cyclised into the pyrazolo-[3,4-e]-as-triazine derivative (4) upon treatment with concentrated sulphuric acid. On the other hand, the pyrazolo[1,5-c]-S-triazine derivative (5) was formed from reaction of 2a with ethanolic sodium ethoxide. 3-Amino-2-pyrazolin-5-one (8) reacted with ethyl acrylate to yield a mixture of the 4-dialkylated derivative (9) and the pyrazolo[3,4-b]pyrone (11). Compound 11 could be converted into the corresponding pyrazolo[3,4-b]pyrones (12) and (13) by the action of acetic acid hydrochloric acid mixture and of concentrated sulphuric acid, respectively.

Pyrimidine Derivatives and Related Compounds, V Synthesis of Some Isoxazolo [2,3-a] pyrimidines. A New Ring System

3-Amino-5-phenyl-4-phenylazoisoxazole (1) reacts with ethyl acetoacetate to yield the corresponding ethyl isoxazolylaminocrotonate derivative (2) which could be thermally cyclized into the isoxazolopyrimidine derivative (4). On the other hand, condensation of 1 with ethoxymethylenemalononitrile has resulted in the formation of the aminoethylene derivative (5). Compound 1 reacted with acrylonitrile to yield the isoxazolo[2,3-a]pyrimidine derivative (6). The latter was converted into the corresponding exo derivative (8) by the action of acetic acid-hydrochloric acid mixture. Compound 1 also reacted with methoxycarbonyl-, ethoxycarbomyl- and benzoyl isothiocyanates to yield the isoxazolylthioureas (10a, b) and (11), respectively. The reaction of 2 with acetic acid-hydrochloric acid and with phenylhydrazine is reported.