138597-12-3

Upstream product

• 19362-96-0 2-(1-hydroxybenzyl)acrylonitrile 
• 108-24-7 acetic anhydride 
• 100-52-7 benzaldehyde 
• 75-36-5 acetyl chloride 
• 107-13-1 acrylonitrile 

Downstream Products

• 26157-51-7 (Z)-2-methyl-3-phenyl-2-propenenitrile 
• 130889-08-6 (Z)-2-(diethoxyphosphorylmethyl)-3-phenylprop-2-enenitrile 
• 130889-09-7 (E)-2-(diethoxyphosphorylmethyl)-3-phenylprop-2-enenitrile 
• 177838-08-3 (2E)-2-(Acetoxymethyl)-3-phenylprop-2-enenitrile 
• 85520-67-8 (Z)-2-ethyl-3-phenylpropenenitrile 
• 58260-82-5 (E)-2-pentyl-3-phenylprop-2-enenitrile 
• 924658-67-3 2-[(4-chloro-phenylamino)-phenyl-methyl]-acrylonitrile 
• 903563-87-1 2-aminomethyl-3-phenylacrylonitrile 
• 1141875-56-0 C₁₃H₁₄N₂O₂ 

Relevant academic research and scientific papers

Crystal Structure of N-(2-Cyano-1-Phenylprop-2-en-1-yl)-4-Methylbenzenesulfonamide

New allylsulfonamide is prepared in a four-step synthetic route: the Morita-Baylis-Hillman adduct prepared from benzaldehyde and acrylonitrile is acetylated using acetic anhydride and DMAP. The acetylated product reacts with DABCO displaced by the additio

Modular and Stereoselective Approach to Highly Substituted Indole/Pyrrole-Fused Diazepanones

A one-pot synthetic method for indole/pyrrole-fused 1,4-diazepanone scaffolds has been developed. This method involves a sequential amide coupling/intramolecular aza-Michael addition of 1H-indole/pyrrole-2-carboxylic acids with Morita-Baylis-Hillman-deriv

A one-pot three-step multicomponent synthesis of functionalized allyl dithiocarbamates using Baylis–Hillman reaction

A one-pot, pseudo five-component, highly diastereoselective, and mild procedure for the synthesis of functionalized allyl dithiocarbamates is developed. The Baylis–Hillman (BH) reaction of aromatic (heteroaromatic) aldehydes and activated alkenes using DA

Enzymatic kinetic resolution of Morita-Baylis-Hillman acetates

Racemic Morita-Baylis-Hillman adducts derived from the reaction of acrylonitrile with benzaldehyde, cinnamaldehyde and hydrocinnamaldehyde have been successfully resolved by means of enzymatic kinetic resolution. The (+)-alcohol products were isolated wit

One-pot synthesis of allyl thioacetate from benzaldehydes and activated alkenes using the Morita-Baylis-Hillman reaction as a key step

An efficient, regioselective and steresoselecitive one-pot protocol for the synthesis of (Z)-S-2-alkoxycarbonyl-3-acylallyl ethanethioates and (E)-S-2-cyano-3-acylallyl ethanethioates from benzaldehydes and activated alkenes (methyl acrylate and acrylonit

2-Azetidinones: Synthesis and biological evaluation as potential anti-breast cancer agents

A series of twenty-five 2-azitidinone (β-lactam) derivatives were synthesized and evaluated for anti-cancer properties against breast cancer, MCF-7 and MDA-MB-231. These β-lactam derivatives depicted significant cytotoxicity in cancer cell lines but not i

N-bromosuccinimide-mediated radical cyclization of 3-arylallyl azides: Synthesis of 3-substituted quinolines

Visible light irradiation of N-bromosuccinimide serves as an effective means to convert methyl 2-(azidomethyl)-3-arylpropenoates and 2-(azidomethyl)-3-arylacrylonitriles to the corresponding iminyl radicals via ?±-hydrogen abstraction and subsequent extrusion of dinitrogen. Thus formed iminyl radicals then undergo intramolecular ortho attack on the aryl ring, affording methyl quin-oline-3-carboxylates and quinoline-3-carbonitriles respectively.

Probing the mechanism of allylic substitution of morita-baylis- Hillman acetates (MBHAS) by using the silyl phosphonite paradigm: Scope and applications of a versatile transformation

A P-C bond-forming reaction between silyl phosphonites and Morita-Baylis-Hillman acetates (MBHAs) is explored as a general alternative towards medicinally relevant ?2;-carboxyphosphinic structural motifs. Conversion rates of diversely substituted MBHAs to phosphinic acids 9 or 14that were recorded by using 31P NMR spectroscopy revealed unexpected reactivity differences between ester and nitrile derivatives. These kinetic profiles and DFT calculations support a mechanistic scenario in which observed differences can be explained from the "lateness" of transition states. In addition, we provide experimental evidence suggesting that enolates due to initial P-Michael addition are not formed. Based on the proposed mechanistic scenario in conjunction with DFT calculations, an interpretation of the E/Z stereoselectivity differences between ester and nitriles is proposed. Synthetic opportunities stemming from this transformation are presented, which deal with the preparation of several synthetically capricious phosphinic building blocks, whose access through the classical P-Michael synthetic route is not straightforward.

Pd-catalyzed decarboxylative allylic coupling of acetates of Baylis-Hillman alcohols with propiolic acids: A highly regio- and stereoselective synthesis of 1,5-diarylpent-1-en-4-yne derivatives

Pd-catalyzed decarboxylative allylic coupling of acetates of Baylis-Hillman alcohols with alkynyl carboxylic acids leading to the formation of an important class of 1,5-diarylpent-1-en-4-ynes in a highly regio- and stereoselective manner has been develope

A facile, versatile, and mild morita-baylis-hillman-type reaction for the modular one-pot synthesis of highly functionalized MBH adducts

Morita-Baylis-Hillman derivatives have been extensively investigated as intermediates in the preparation of important classes of compounds. However, there are intrinsic limitations regarding the structure of the Michael electrophile acceptors, the aldehydes, and the catalysts. Therefore, this transformation has several drawbacks, including, for example, its long reaction times. Herein we present a simple, general, fast, and high-yielding protocol for the one-pot synthesis of Morita-Baylis-Hillman derivatives. Our approach is driven by a lithium selenolate Michael/aldol operation with concomitant O-functionalization/selenoxide elimination cascade sequences. Here we describe a one-pot, fast, and high-yielding methodology for the synthesis of different Morita-Baylis-Hillman derivatives by a four-component cascade reaction. The cascade is based on a Michael/aldol/O-functionalization/selenoxide elimination sequence. This protocol completely avoids the manipulation of selenium species with an unpleasant odor.