1-Bis(methoxy)-4-bis(methylthio)-3-buten-2-one: useful three carbon synthon for synthesis of five and six membered heterocycles with masked (or unmasked) aldehyde functionality

Mahata, Pranab Kumar; Kumar, U. K. Syam; Sriram, V; Ila, H.; Junjappa, H.

doi:10.1016/s0040-4020(03)00332-6

Cited by 35 publications

(26 citation statements)

References 38 publications

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“…Mahata e colaboradores, 6 em 2003, sintetizaram o 4,4-dimetil-1,1-dimetoxi-3-buten-2-ona 7 a partir da reação do enolato do piruvaldeído dimetilacetal 6 com o CS 2 e iodeto de metila, obtendo o produto com 85% de rendimento (Esquema 4). A reação ocorre através do ataque do enolato (formado pela perda do próton da metila α à carbonila do piruvaldeído dimetilacetal) ao carbono parcialmente positivo do CS 2 , seguida de alquilação dos dois átomos de enxofre pelo iodeto de metila.…”

Section: Síntese De α-Oxoceteno Ditioacetais a Partir De Compostos Caunclassified

“…Explorando o potencial sintético do composto 7, o 2-(tiometil) tiofen-4-il]carbaldeído 49 foi obtido a partir de uma suspensão Zn-Cu em éter seco e cristais de iodo (Esquema 18), 6 condições reacionais semelhante às utilizadas por Bhat e colaboradores 30 na síntese de uma gama de tiofenos derivados de α-oxoceteno ditioacetais.…”

Section: Síntese De Tiofenosunclassified

“…O 5-aminoisoxazol 57 e o 5-aminopirazol 58 foram obtidos através da reação da enaminona 56 com hidroxilamina e hidrazina, respectivamente (Esquema 22). 6 As reações levaram à formação exclusiva dos aminoazóis com a eliminação de tiometanol.…”

Section: Síntese De Isoxazóis E Pirazóisunclassified

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Aplicação de α-oxoceteno ditiocetais em síntese orgânica

Siqueira¹,

Neuenfeldt²,

Duarte³

et al. 2010

Quím. Nova

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Recebido em 16/7/09; aceito em 1/10/09; publicado na web em 10/3/10 REACTIVITY OF α-OXOKETENE DITHIOCETALS IN ORGANIC SYNTHESIS. The synthesis and reactivity of α-oxoketenes dithioacetals (S,S-acetals), general structure [(R¹C=OC(R²)=C(SR³) (SR 4 )], are reported. We also showed the application of S,S acetals as synthons for efficient synthesis of isoxazoles, pyrazoles, indazoles, thiophenes, dithiol thiones, pyridines, pyrimidines and other heterocycles. This work aims to review the importance of α-oxoketenes dithioacetals in organic chemistry during the past few years.

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Section: Síntese De α-Oxoceteno Ditioacetais a Partir De Compostos Caunclassified

Section: Síntese De Tiofenosunclassified

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Aplicação de α-oxoceteno ditiocetais em síntese orgânica

Siqueira¹,

Neuenfeldt²,

Duarte³

et al. 2010

Quím. Nova

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“…Now a days of literature have been reported for the synthesis of thiophene, furan, isooxazole, pyrazole, pyridine and pyrimidine etc. heterocycles by using dithioacetal in place of aldehyde [11,12]. Thus, above literature promote us to synthesize novel pyrimidine analogues using ketene dithioacetal and their biological screening.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Fully Substituted Pyrimidines by Using Ketene Dithioacetal as Potent Antimicrobial Agent

Khunt

Pipaliya

Ghelani

et al. 2013

ILCPA

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Various ketene dithioacetals of acetoacetanilides were reacted with guanidine nitrate in the presence of base to produce the 2-amino-4-isopropyl-6-alkoxy-N-arylpyrimidine-5-carboxamide derivatives with good yields. All the synthesized compounds were characterized by mass, NMR and IR and also evaluated for antimicrobial activity against five different bacterial and fungal strains. The compounds 4i, 4k and 4l has found comparatively good active against all the bacterial strains.

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“…Then, the reaction mixture was refluxed for 24 h to complete the reaction. The work-up procedure was conducted as stated in the literature 5 to yield I as the major product in 75% yield (white solid, mp 129 -131˚C), Fig. 1.…”

mentioning

confidence: 99%