74198-48-4

Upstream product

• 85-44-9 phthalic anhydride 

Downstream Products

• 927836-37-1 (2Z)-2-{N-[(S)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-4-methylthiobutyryl]-N-mesitylaminomethylidene}benzo[b]thiophen-3(2H)-one 
• 927836-36-0 (2Z)-2-{N-[(S)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-4-methylthiobutyryl]-N-(4-iodophenyl)aminomethylidene}benzo[b]thiophen-3(2H)-one 

Relevant academic research and scientific papers

1,2-Hydride Migration in Dialkyl α-Diazophosphonates Catalyzed by [Cu(MeCN)4]PF6: A Novel Approach to β-Amino (E)-Enylphosphonates

The regiospecific and stereoselective 1,2-migration reaction of dialkyl α-diazophosphonates for the synthesis of β-amino (E)-enylphosphonates is developed utilizing tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)4PF6] as the catalyst and N,N-dimethylformamide as an additive. A possible mechanism for the 1,2-migration reaction involving a metal carbene is presented. An investigation on the E/Z isomer selectivity of this process demonstrates that steric factors play an important role on the outcome. This process provides a straightforward access to β-amino (E)-enylphosphonates in moderate to good yields.

Trifluoroborane-catalyzed C-H functionalization/S-H insertion reaction: Construction of N,S-acetal quaternary centers

Abstract The trifluoroborane-catalyzed C-H functionalization/S-H insertion reaction of α-diazophosphonates with thiols has been developed. A plausible reaction mechanism has been proposed to understand the combined reaction. This process provides straightforward access to N,S-acetals containing quaternary centers in moderate to good yields and chemoselectivity.

Unexpected stereoselective synthesis of (Z)-β-alkenyl substituted β-amino phosphonates through β,γ-dihydrogen shift reaction catalyzed by a copper(I) complex and iodine [Cu(MeCN)4]PF 6/I2

A series of dialkyl a-diazophosphonates has been prepared from natural amino acids. The diazo decomposition of these diazophosphonate compounds with tetrakis(acetonitrile)copper(I) hexafluorophosphate/iodine, [Cu(MeCN) 4]PF6/I2, as catalyst has been investigated. It was found that the diazo decomposition of dialkyl a-diazophosphonates gave a mixture of β,γ-dihydrogen shift and 1,2-hydride migration products and afforded β-alk- enyl-substituted β-amino phosphonates with the Z configuration. The mechanism of this novel diazo decomposition process was discussed.

Chiron based synthesis of isocoumarins: Reactivity of α-substituted carboxylic acids

The asymmetric synthesis of a novel (S)-isocoumarin has been attempted in a single step by the coupling of homophthalic acid with (S)-N-protected amino acids and α-chloroacids at high temperature by exploiting a chiral pool methodology. The coupling of homophthalic acid with N-protected (S)-amino acids gave exclusion of the carboxyl/alkyl group. However, coupling of homophthalic acid with α-chloroacids afforded asymmetric isocoumarins in high yield.