1607804-80-7

Upstream product

• 106824-46-8 4,5-dimethoxy-2-(2-phenylethynyl)benzaldehyde 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 536-74-3 phenylacetylene 
• 110451-87-1 2-bromomethyl-1-iodo-4,5-dimethoxybenzene 
• 54370-00-2 2-bromo-4,5-dimethoxybenzyl alcohol 

Downstream Products

• 1607804-85-2 6,7-dimethoxy-3-(4-methoxyphenyl)-2-phenylisoquinolin-1(2H)-one 
• 127141-20-2 (Z)?1?benzylidene?5,6?dimethoxy?1,3?dihydroisobenzofuran 

Relevant academic research and scientific papers

Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions

An efficient, transition-metal-free method to synthesize dihydroisobenzofuran derivatives via intramolecular hydroalkoxylation of aromatic alkynols with the promotion of cesium carbonate has been developed. The reaction proceeds regioselectively with exclusive formation of 5-exo-dig product, and only Z-isomer of the new generated double bond is observed. This new protocol features with milder reaction conditions, more convenient operation and satisfactory selectivities.

Construction of Six-Membered Silacyclic Skeletons via Platinum-Catalyzed Tandem Hydrosilylation/Cyclization with Dihydrosilanes

Catalytic silicon-carbon or silicon-heteroatom bond-forming hydrosilylation has become increasingly important in synthetic chemistry, catalysis and organosilicon chemistry. Herein we report a platinum-catalyzed one-pot and tandem hydrosilylation/cyclization of OH-containing alkynes with dihydrosilanes, allowing for facile synthesis of six-membered organosilicon compounds, including silyloxycycles and cyclic siloxanes in high yields and with good stereoselectivities. (Figure presented.).

Selective Divergent Synthesis of Indanols, Indanones, and Indenes via Acid-Mediated Cyclization of (Z)- and (E)-(2-Stilbenyl)methanols and Its Application for the Synthesis of Paucifloral F Derivatives

Starting from bromo/iodobenzaldehyde derivatives, the corresponding (Z)- and (E)-(2-stilbenyl)methanols could be prepared in 2-5 steps via Pd-catalyzed cross-coupling reactions (Sonogashira and Heck reactions) followed by aryllithium/aryl Grignard addition. For the (E)-stilbenes, subsequent acid-mediated cyclization using p-TsOH immobilized on silica (PTS-Si) at low temperatures furnished the 2,3-trans-1-indanols with complete stereocontrol at the C2-C3. Further oxidization of the alcohol provided the indanones, which are structurally related to the natural product paucifloral F. At higher temperatures, 1,2- and 2,3-disubstituted indenes could be selectively prepared in good to excellent yields. On the other hand, the (Z)-stilbenes, under similar conditions (PTS-Si), did not give the indanols; only the 1,2-disubstituted indenes could be obtained. To gain further insights into the stereochemistry at C2-C3 for the (Z)-stilbenes, hydride or azide was employed as a nucleophile; the corresponding indane products were obtained with the cis stereochemistry at the C2-C3. Thus, the (Z)- or (E)-olefin geometry of the substrate directed the stereoselective indanyl cyclization to furnish the cis or trans at the C2-C3 ring junction, respectively, while reaction conditions controlled the selectivity of the product types.

Fused-Ring Formation by an Intramolecular “Cut-and-Sew” Reaction between Cyclobutanones and Alkynes

The development of a catalytic intramolecular “cut-and-sew” transformation between cyclobutanones and alkynes to construct cyclohexenone-fused rings is described herein. The challenge arises from the need for selective coupling at the more sterically hind

Transition metal-free cascade reactions of alkynols to afford isoquinolin-1(2H)-one and dihydroisobenzofuran derivatives

Transition metal-free cascade reactions of alkynols with imines have been achieved using potassium tert-butoxide as catalyst. Switching the reaction solvent gives two kinds of products in good yield: isoquinolin-1(2H)-one derivatives and dihydroisobenzofuran derivatives. This approach was used to generate the natural product 8-oxypseudopalmatine in a two-step procedure from commercially available starting materials. Additionally, multicomponent reactions of alkynols, aldehydes, and amines were also successfully achieved to afford isoquinolin-1(2H)-one derivatives.