Synthesis of Novel Bis-enaminones by KHSO4-assisted Facile Michael Addition-elimination Reaction of 3-(dimethylamino)-1-phenylprop-2-en-1-ones with Diamines in Water

Devi, A. Satyapati; Helissey, Philippe; Vishwakarma, Jai N.

doi:10.4236/gsc.2011.12006

Cited by 6 publications

(7 citation statements)

References 33 publications

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“…Though the enaminone formed by primary amine is commonly recognized as one kind of dynamic bond, 40 little attention has been paid to secondary amine based enaminone, which seems more stable. To Scheme 3A), 41,42 which gave us an inspiration to get exact degradation products by dealing polymers with Lewis acid and primary amine. After optimization, it was found that Fe 3+ can catalyze the reaction of P1a2a with aniline at room temperature, but only 54% of 10 can be separated out.…”

Section: Resultsmentioning

confidence: 99%

Aroylacetylene-Based Amino-Yne Click Polymerization toward Nitrogen-Containing Polymers

Chen

Bai

et al. 2020

Macromolecules

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A highly efficient, spontaneous, and atom-economic polymerization of aroylacetylenes and amines at room temperature in air was established, and poly(β-enaminone)s with high molecular weights were produced in nearly quantitative yields. Moreover, singly E-configuration polymers can be obtained efficiently with secondary amines, while absolute Z-configuration products were prepared when using primary amines. In addition, the poly(β-enaminone)s can be degraded by primary amines in aqueous system to obtain definite compounds, proving their wide application prospects as degradable nitrogen containing polymers. File list (2) download file view on ChemRxiv manuscript.docx (1.14 MiB) download file view on ChemRxiv Supporting Information.pdf (2.80 MiB)

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Section: Resultsmentioning

confidence: 99%

Aroylacetylene-Based Amino-Yne Click Polymerization toward Nitrogen-Containing Polymers

Chen

Bai

et al. 2020

Macromolecules

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“…A similar approach was used for the synthesis of the bis(1,2,3,4‐tetrahydropyrimidines) ( 16a – d ) and 1,2‐bis(5‐benzoyl‐3,6‐dihydro‐2 H ‐1,3‐oxazine‐3‐yl)‐ethane ( 17 ), starting from the previously reported bis (secondary enaminone) 15 , as depicted in Scheme .…”

Section: Resultsmentioning

confidence: 99%

“…Compounds 20a , 20b , 21a , 21b , 22 , 23a , 23b , 24 , and 25 are of limited solubility in common 1 H NMR solvents. Compounds 1 , 2a , 2b , 2c , 3a – 3c , 15 , and 18 were prepared as previously described.…”

Section: Methodsmentioning

confidence: 99%

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Mannich Reaction with Enaminones: Convenient Synthesis of Functionalized Tetrahydro‐pyrimidines, Dihydro‐1,3‐oxazines, and Dihydro‐1,2,4‐triazepines

Afsah

El‐Desoky

Etman

et al. 2018

Journal of Heterocyclic Chem

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A series of tetrahydropyrimidines and bis-(tetrahydropyrimidines) was synthesized by Mannich reaction of sec-emaminones with formaldehyde and the appropriate amine or diamine. Whereas the reaction with formaldehyde gave the dihydro-1,3-oxazine. Tetrahydropyrimidines incorporating a phenolic Mannich base were obtained by Mannich reaction of the appropriate tetrahydropyrimidine. The bis(sec-enaminones) were used as precursors in synthesis of bis(tetrahydropyrimidines) and bis(dihydro-1,3-oxazines). Treatment of the appropriate sec-emaminone or bis(sec-enaminone) with hydrazine hydrate or phenylhydrazine and a suitable aldehyde afforded dihydro-1,2,4-triazepines and the bis(dihydro-1,2,4-triazepines). Scheme 2. Synthesis of the phenolic Mannich bases 8, 9, and 11. Scheme 3. Synthesis of bis(tetrahydropyrimidines) (13a-f and 16a-d) and bis(dihydro-1,3-oxazines) (14 and 17).Scheme 4. Synthesis of bis(tetrahydropyrimidines) (20a-b and 21a-b) and bis(dihydro-1,3-oxazine) (22).

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“…In continuation with our efforts for the development of novel synthetic strategies assisted by KHSO 4 [42,43], we report herein a facile environment-friendly, one-pot two-step regioselective synthesis for 3,7-diarylpyrazolo[1,5-a]pyrimidines related to zaleplon and 3,6-diarylpyrazolo[1,5-a]pyrimidin-7-amines.…”

Section: Introductionmentioning

confidence: 98%

A facile environment-friendly one-pot two-step regioselective synthetic strategy for 3,7-diarylpyrazolo[1,5-a]pyrimidines related to zaleplon and 3,6-diarylpyrazolo[1,5-a]pyrimidine-7-amines assisted by KHSO $$_{4}$$ 4 in aqueous media

2015

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3-Aminopyrazoles required for the synthesis of pyrazolo[1,5-a]pyrimidines were obtained by the reaction of enaminonitriles with hydrazine hydrate. The resulting aminopyrazoles are reacted with formylated acetophenones under reflux at [Formula: see text] assisted by KHSO[Formula: see text] in aqueous media to form regioselectively 3,7-diarylpyrazolo[1,5-a]pyrimidines and 3,6-diarylpyrazolo[1,5-a]pyrimidine-7-amines. X-ray crystallography of selected compounds 5b and 7i further confirmed the regioselective formation of these products.

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Synthesis of Novel Bis-enaminones by KHSO4-assisted Facile Michael Addition-elimination Reaction of 3-(dimethylamino)-1-phenylprop-2-en-1-ones with Diamines in Water

Cited by 6 publications

References 33 publications

Aroylacetylene-Based Amino-Yne Click Polymerization toward Nitrogen-Containing Polymers

Aroylacetylene-Based Amino-Yne Click Polymerization toward Nitrogen-Containing Polymers

Mannich Reaction with Enaminones: Convenient Synthesis of Functionalized Tetrahydro‐pyrimidines, Dihydro‐1,3‐oxazines, and Dihydro‐1,2,4‐triazepines

A facile environment-friendly one-pot two-step regioselective synthetic strategy for 3,7-diarylpyrazolo[1,5-a]pyrimidines related to zaleplon and 3,6-diarylpyrazolo[1,5-a]pyrimidine-7-amines assisted by KHSO $$_{4}$$ 4 in aqueous media

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