101220-34-2

Upstream product

• 614-16-4 Benzoylacetonitrile 
• 100-52-7 benzaldehyde 
• 645-59-0 dihydrocinnamonitrile 
• 35572-06-6 2-benzyl-3-(phenyl)-3-oxopropanenitrile 
• 93-89-0 benzoic acid ethyl ester 

Downstream Products

• 86625-29-8 1,2-Dihydro-4,6-diphenyl-2-thioxo-3,5-pyridinedicarbonitrile 
• 86625-34-5 4,4',6,6'-Tetraphenyl-2,2'-dithiobis(3,5-pyridinedicarbonitrile) 
• 75238-88-9 3-carbamoyl-5-cyano-6-hydroxy-4,6-diphenylpiperidin-2-one 
• 86625-39-0 2-Methylthio-4,6-diphenyl-3,5-pyridinedicarbonitrile 
• 75238-80-1 3,4-dicyano-6-hydroxy-4,6-diphenyl-piperidin-2-one 
• 90699-77-7 3-hydroxycyclohexanone 

Relevant academic research and scientific papers

One-pot highly diastereoselective annulation to N-unprotected tetrasubstituted 2-pyrrolines

A one-pot DABCO-catalysed Michael addition of glycine imine-derived esters to trans-2-aroyl-3-arylacrylonitriles followed by a deprotection/cyclization/tautomerization sequence afforded tetrasubstituted N-unprotected trans-2-pyrrolines in up to 96% yield.

Reduced graphene oxide supported piperazine in aminocatalysis

Reduced graphene oxide (rGO) has been used as a support for piperazine to provide a heterogeneous bifunctional organocatalyst (rGO-NH) that is able to efficiently promote vintage organic transformations such as Knoevenagel, Michael and aldol reactions. The obtained results suggest a significant role of the support in the course of these reactions. This journal is the Partner Organisations 2014.

IBX-mediated dehydrogenation of substituted β-oxonitriles

A convenient method for the mild dehydrogenation of β-oxonitriles is presented. When treated with o-iodoxybenzoic acid (IBX), a range of these compounds were transformed into their unsaturated counterparts. Furthermore, we show that the products of the dehydrogenation can react in situ, undergoing rapid hetero-Diels-Alder reactions with enol ethers to give multiply substituted dihydropyrans. We also describe the dehydrogenation of cyclic β-oxonitriles, which leads to the formation of substituted phenols. Copyright

Asymmetric synthesis of trisubstituted tetrahydrothiophenes bearing a quaternary stereocenter via double michael reaction involving dynamic kinetic resolution

The stereoselective synthesis of highly functionalized tetrahydrothiophenes bearing three contiguous stereocenters, one of them quaternary, can be achieved by reacting trans-α-cyano-α,β-unsaturated ketones and trans-tert-butyl 4-mercapto-2-butenoate in the presence of a readily available amine thiourea. The products are obtained in high yield, good diastereoselectivity, and excellent enantioselectivity. The overall formation of tetrahydrothiophenes occurs via a cascade double Michael reaction involving a highly efficient process of dynamic kinetic resolution.

Microwave synthesis of α-cyano chalcones

A novel methodology for facile production of α-cyano chalcones under microwave irradiation is described. Utilizing a Knoevenagel condensation between benzoylacetonitriles and aromatic aldehydes, substituted chalcones are generated via a 15-min, one-pot synthesis. Diversification of aromatic groups, including electron-withdrawing, electron-donating, and heterocyclic substitutions, has led to the isolation of over twenty colored, solid chalcone products. Furthermore the methodology can be extended to the synthesis of benzylidenemalononitriles as well as methyl and ethyl α-cyano cinnamates.

Tandem cross-Rauhut-Currier/cyclization reactions of activated alkenes to give densely functionalized 3,4-dihydropyrans

A novel tandem cross-Rauhut-Currier/cyclization reaction between α,β-unsaturated ketones was developed. Using DABCO (20 mol %) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative catalytic cycle was proposed with key intermediates confirmed by ESIMS studies.

Enantioselective nitrocyclopropanation of α,β-unsaturated α-cyanoimides catalyzed by bifunctional thiourea

The organocatalyzed asymmetric cyclopropanation of bromonitromethane with α-cyano-α,β-unsaturated imides is described. In addition, the same bifunctional thiourea was revealed to be a powerful catalyst for preparing these α-cyanoimides by Knoevenagel condensation. Georg Thieme Verlag Stuttgart.

Efficient synthesis of 4-cyano 2,3-dihydrooxazoles by direct amination of 2-alkylidene 3-oxo nitriles

The addition of N-protected O-sulfonyl hydroxylamine derivatives on 2-alkylidene 3-oxo nitrites gives 2,5-disubstituted 4-cyano 2,3-dihydrooxazoles (4-oxazolines) by a practical and efficient synthetic procedure under very mild conditions in high yields. Likely, the formation of N,O-heterocycles proceeds through a domino reaction involving a fast rearrangement of unstable 2-acyl 2-cyano aziridines. Georg Thieme Verlag Stuttgart.

Pyridine Syntheses. II. Condensation Routes Toward Streptonigrin Ring C [1]

Alternative complimentary syntheses of penta-substituted pyridine rings with full regiochemical control of substituents were studied as a method for the synthesis of Streptonigrin (1). Various α-substituted acetophenones 2 were reacted with enones 3 in acetic acid/ammonium acetate and air to afford penta-substituted pyridines 4. α-Substituents that could provide a source of exocyclic nitrogen at position 3 of these Steptonigrin ring-C models proved to be the limiting factor. However, an inverse "3+2+1" cyclocondensation of α-cyanochalcone 5c with 2-furyl ethyl ketone (6b) afforded the desired model 6-(2-furyl)-5-methyl-2,4-diphenyl-3-pyridinecarbonitrile (4g) in 75% yield.

Hetero-Diels-Alder Reaction of 3-Aryl-2-benzoyl-2-propenenitriles with Enol Ethers. Synthesis of 2-Alkoxy-3,4-dihydro-2H-pyran-5-carbonitriles

The hetero-Diels-Alder reaction of 3-aryl-2-benzoyl-2-propenenitriles 1a-d with enol ethers 2a-c yields cis/trans diastereoisomers of 2-alkoxy-4,6-diaryl-3,4-dihydro-2H-pyran-5-carbonitriles 3 and 4 in 79-98% yield. The similar reaction of 1a-c with cyclic enol ether 5 affords diastereoisomeric cycloadducts 6 and 7 with cis annulated pyran rings. Reaction of 3 with sulfuric acid leads to 2-hydroxy-3,4-dihydro-2H-pyran-5-carbonitriles 8 and 9.