936916-82-4

Upstream product

• 37614-59-8 4-(4-methoxyphenyl)prop-2-yn-1-ol 
• 106-96-7 propargyl bromide 
• 6921-27-3 dipropargyl ether 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 696-62-8 para-iodoanisole 

Downstream Products

• 936916-72-2 1,7-bis(4-methoxyphenyl)-4-oxahepta-1,6-diyne 
• 1599470-96-8 1-benzyl-4-(3-(3-(4-methoxyphenyl)prop-2-ynyloxy)prop-1-ynyl)-3-methyl-1H-imidazol-2(3H)-one 

Relevant academic research and scientific papers

Heat Versus Basic Conditions: Intramolecular Dehydro-Diels-Alder Reaction of 1-Indolyl-1,6-heptadiynes for the Selective Synthesis of Substituted Carbazoles

The intramolecular dehydro-Diels-Alder reaction of 1-indolyl-1,6-heptadiynes proceeds smoothly under rather mild heating conditions to give substituted carbazoles in moderate to good yields. The reaction of 7-aryl-1-indolyl-1,6-heptadiynes under heating gives the corresponding carbazoles chemoselectively in high yields, whereas the reaction under basic conditions gives naphthalenes as major products.

Synthesis of phthalides from bis-propargyl ethers: Use of Garratt-Braverman cyclization to construct the phthalans and IBX as a new reagent for subsequent oxidation

An efficient route to phthalides is described starting from easily available bis-propargyl ethers. The method involves Garratt-Braverman cyclization of the ethers to phthalans which are then efficiently oxidized to the phthalides by iodoxy benzoic acid (IBX) which has been shown to be a superior reagent in terms of yield and reagent stoichiometry for such a transformation in comparison with more commonly used KMnO4/CuSO4 reagent.

Intramolecular anionic Diels-Alder reactions of 1-aryl-4-oxahepta-1,6-diyne systems in DMSO

Base-promoted cycloaddition reactions of 1-aryl- or 1-aryl-7-substituted-4- oxahepta-1,6-diyne systems in DMSO have proven to involve an anionic intramolecular Diels-Alder process taking place even at room temperature in spite of the reaction suffering from temporary disruption of aromaticity. Although initially formed α-arylallenide anion can be protonated by DMSO, it can be back to the allenide anion probably because of a small acidity difference between α-arylallene and DMSO. The α-arylallenide anion in combination with the α-aryl substituent can constitute an anionic diene structure that undergoes the intramolecular Diels-Alder reaction involving the C(6)-yne part, a very fast process probably because of the increased HOMO-1 level of the anionic diene, as shown by DFT calculations. Diversified substituted naphthalenes, benzofurans, phenanthrenes, and quinolines, including biaryl architectures, are available from 4-oxahepta-1,6-diynes in a highly expeditious way.