New Selective Synthesis of Dimethyl 3-Alkylamino Itaconates

Arfaoui, A.; Beji, Feten; Ayed, Taı̈cir Ben

doi:10.1080/00397910802213786

Cited by 7 publications

(1 citation statement)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It was considered as the most successful pathway for carbon–heteroatom bond formation . Considering the importance of CN bonding creation in organic synthesis and in connection with our research projects aimed to develop new routes to α‐functional allylamines , we report herein the behavior of diethyl ( E )‐1‐(bromomethyl)‐2‐cyanovinylphosphonate 1 as a powerful Michael acceptor , toward secondary and tertiary amines as a source of N ‐nucleophilic reagents.…”

Section: Introductionmentioning

confidence: 99%

Selected Reactions of Diethyl (E)‐1‐(bromomethyl)‐2‐cyanovinylphosphonate with Secondary and Tertiary Amines

Fray

Kraïem

2013

Heteroatom Chemistry

Self Cite

View full text Add to dashboard Cite

An easy regio‐ and stereoselective synthesis of new nitrogenous molecules 2a–e was successfully realized via an effective coupling reaction of diethyl (E)‐1‐(bromomethyl)‐2‐cyanovinylphosphonate 1 with various secondary amines in methanol. Hence, the use of less and more bulky secondary amines gives rise, respectively, to the successive (SN2′) substitution–isomerization and (SN2) substitution derivatives 2a–c and 2d–e. Moreover, the addition of tertiary amines to 1 in the same reaction conditions, leads exclusively to the rearranged vinyl ether 3 in good yields.

show abstract

Section: Introductionmentioning

confidence: 99%

Selected Reactions of Diethyl (E)‐1‐(bromomethyl)‐2‐cyanovinylphosphonate with Secondary and Tertiary Amines

Fray

Kraïem

2013

Heteroatom Chemistry

Self Cite

View full text Add to dashboard Cite

show abstract

S_N2’ versus S_N2 Reactivity: Control of Regioselectivity in Conversions of Baylis–Hillman Adducts

Baidya

Remennikov

Mayer

et al. 2010

Chemistry A European J

View full text Add to dashboard Cite

TiCl(4)-induced Baylis-Hillman reactions of alpha,beta-unsaturated carbonyl compounds with aldehydes yield the (Z)-2-(chloromethyl)vinyl carbonyl compounds 5, which react with 1,4-diazabicyclo[2.2.2]octane (DABCO), quinuclidine, and pyridines to give the allylammonium ions 6. Their combination with less than one equivalent of the potassium salts of stabilized carbanions (e.g. malonate) yields methylene derivatives 8 under kinetically controlled conditions (S(N)2' reactions). When more than one equivalent of the carbanions is used, a second S(N)2' reaction converts 8 into their thermodynamically more stable allyl isomers 9. The second-order rate constants for the reactions of 6 with carbanions have been determined photometrically in DMSO. With these rate constants and the previously reported nucleophile-specific parameters N and s for the stabilized carbanions, the correlation log k (20 degrees C)=s(N + E) allowed us to calculate the electrophilicity parameters E for the allylammonium ions 6 (-19 < E < -18). The kinetic data indicate the S(N)2' reactions to proceed via an addition-elimination mechanism with a rate-determining addition step.

show abstract

ChemInform Abstract: New Selective Synthesis of Dimethyl 3‐Alkylamino Itaconates.

Arfaoui¹,

Beji²,

Ayed³

2009

ChemInform

View full text Add to dashboard Cite

Aminocarboxylic acids (hydrazinocarboxylic acids) and esters P 0270New Selective Synthesis of Dimethyl 3-Alkylamino Itaconates. -The title compounds, e.g. (III), are obtained via reaction of an intermediate DABCO ammonium salt with amines. In the presence of bulky secondary or tertiary amines, reaction of the salt with the solvent leads to product (V). -(ARFAOUI, A.; BEJI, F.; AYED, T. B.; AMRI*, H.; Synth.

show abstract

New Selective Synthesis of Dimethyl 3-Alkylamino Itaconates

Cited by 7 publications

References 23 publications

Selected Reactions of Diethyl (E)‐1‐(bromomethyl)‐2‐cyanovinylphosphonate with Secondary and Tertiary Amines

Selected Reactions of Diethyl (E)‐1‐(bromomethyl)‐2‐cyanovinylphosphonate with Secondary and Tertiary Amines

S_N2’ versus S_N2 Reactivity: Control of Regioselectivity in Conversions of Baylis–Hillman Adducts

ChemInform Abstract: New Selective Synthesis of Dimethyl 3‐Alkylamino Itaconates.

Contact Info

Product

Resources

About

New Selective Synthesis of Dimethyl 3-Alkylamino Itaconates

Cited by 7 publications

References 23 publications

Selected Reactions of Diethyl (E)‐1‐(bromomethyl)‐2‐cyanovinylphosphonate with Secondary and Tertiary Amines

Selected Reactions of Diethyl (E)‐1‐(bromomethyl)‐2‐cyanovinylphosphonate with Secondary and Tertiary Amines

SN2’ versus SN2 Reactivity: Control of Regioselectivity in Conversions of Baylis–Hillman Adducts

ChemInform Abstract: New Selective Synthesis of Dimethyl 3‐Alkylamino Itaconates.

Contact Info

Product

Resources

About

S_N2’ versus S_N2 Reactivity: Control of Regioselectivity in Conversions of Baylis–Hillman Adducts