1245321-64-5

Upstream product

• 108-24-7 acetic anhydride 
• 103890-70-6 2-(diethoxymethyl)benzaldehyde 
• 35822-58-3 2-bromobenzaldehyde diethyl acetal 
• 132233-84-2 2-(dimethoxymethyl)benzaldehyde 
• 4301-14-8 acetylenemagnesium bromide 
• 35849-09-3 o-bromobenzaldehyde dimethyl acetal 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 1617527-03-3 1-ethynyl-2-(4-fluorophenyl)isoindoline 
• 1617527-01-1 1-ethynyl-2-phenylisoindoline 
• 1617526-95-0 1-(2-((phenylamino)methyl)phenyl)prop-2-yn-1-yl acetate 
• 1617526-96-1 1-(2-(((4-methylphenyl)amino)methyl)phenyl)prop-2-yn-1-yl acetate 
• 1617527-02-2 1-ethynyl-2-(4-methylphenyl)isoindoline 
• 1617526-97-2 1-(2-(((4-fluorophenyl)amino)methyl)phenyl)prop-2-yn-1-yl acetate 
• 1617527-04-4 2-(4-bromophenyl)-1-ethynylisoindoline 
• 1617526-98-3 1-(2-(((4-bromophenyl)amino)methyl)phenyl)prop-2-yn-1-yl acetate 
• 1333077-95-4 1-(2-((2-tosylhydrazono)methyl)phenyl)prop-2-ynyl acetate 
• 1333078-41-3 ethyl 9-methoxy-6-(methoxymethoxy)-5-methylpyrazolo[5,1-a]isoquinoline-1-carboxylate 
• 1333078-14-0 5-methyl-1-phenylpyrazolo[5,1-a]isoquinolin-6-yl acetate 

Relevant academic research and scientific papers

Copper-Catalyzed One-Pot Cascade Cyclization for the Synthesis of Isoindolo[2,1-a]quinoxalines

A copper-catalyzed one-pot cascade cyclization of 2-(1-(acetyloxy)propargyl)benzaldehydes with o-phenylenediamines for an access to substituted isoindolo[2,1-a]quinoxalines has been developed. The reaction features readily available starting materials, simple operational procedure, and broad substrate scopes. Under optimal conditions, various isoindolo[2,1-a]quinoxalines were afforded in 41–88% yields. (Figure presented.).

Construction of complex bisether-bridged medium-sized cyclic compounds from o-(1-(acyloxy)propargyl)benzaldehydes under base and acid catalysis

We report herein our serendipitous discovery of the rapid and straightforward accesses to unprecedented diverse complex molecular structures from readily available starting materials. Catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene under mild conditions, o-(1-(acyloxy)propargyl)benzaldehydes 1 underwent efficient and selective dimerization reactions to produce novel complex bisether-bridged tricyclic products 3 and 4. The reactions proceeded most probably through dimerizations between 3-methylene-3H-isochromene intermediate and its zwitterionic resonance structures which were generated from a concerted 6-πelectrocyclic ring closure reaction from the initially formed (2-formylphenyl)allene intermediates derived directly from o-(1-(acyloxy)propargyl)benzaldehydes. Treatment of the resulting product simply with NaOEt in ethanol and aqueous HCl, respectively, enabled further development of complex molecular diversities.

Enantioselective intramolecular propargylic amination using chiral copper-pybox complexes as catalysts

Intramolecular propargylic amination of propargylic acetates bearing an amino group at the suitable position in the presence of chiral copper-pybox complexes proceeds enantioselectively to give optically active 1-ethynyl-isoindolines (up to 98% ee). The method described in this communication provides a useful synthetic approach to the enantioselective preparation of nitrogen containing heterocyclic compounds with an ethynyl group at the α-position. This journal is the Partner Organisations 2014.