104571-72-4Relevant academic research and scientific papers
Tandem buildup of complexity of aromatic molecules through multiple successive electrophile generation in one pot, controlled by varying the reaction temperature
Sumita, Akinari,Otani, Yuko,Ohwada, Tomohiko
supporting information, p. 1680 - 1693 (2016/02/09)
While some sequential electrophilic aromatic substitution reactions, known as tandem/domino/cascade reactions, have been reported for the construction of aromatic single skeletons, one of the most interesting and challenging possibilities remains the one-pot build-up of a complex aromatic molecule from multiple starting components, i.e., ultimately multi-component electrophilic aromatic substitution reactions. In this work, we show how tuning of the leaving group ability of phenolate derivatives from carbamates and esters provides a way to successively generate multiple unmasked electrophiles in a controlled manner in one pot, simply by varying the temperature. Here, we demonstrate the autonomous formation of up to three bonds in one pot and formation of two bonds arising from a three-component electrophilic aromatic substitution reaction. This result provides a proof-of-concept of our strategy applicable for the self-directed construction of complex aromatic structures from multiple simple molecules, which can be a potential avenue to realize multi-component electrophilic aromatic substitution reactions.
Novel thiophene derivatives, their process of preparation and the pharmaceutical compositions which comprise them
-
Page/Page column 19, (2010/11/30)
A compound of formula (I) selected from: wherein: X represents oxygen or sulphur, Y represents oxygen, —NH— or —N(C1-C6)alkyl-, Ra represents hydrogen, halogen, (C1-C3)alkyl, hydroxyl or (C1-C3)alkoxy, Rb represents hydrogen, halogen or (C1-C3)alkyl, A represents phenyl, pyridyl, (C5-C6)cycloalkyl or (C5-C6)cycloalkenyl, R1 and R2 each represent a group selected from hydrogen, halogen, cyano, nitro, haloalkyl, haloalkoxy, alkyl, alkenyl, alkynyl, —OR4, —NR4R5, —S(O)nR4, —C(O)R4, —CO2R4, —O—C(O)R4, —C(O)NR4R5, —NR5—C(O)R4, —NR5—SO2R4, -T-CN, -T-OR4, -T-OCF3, -T- NR4R5, -T-S(O)nR4, -T-C(O)R4, -T-CO2R4, -T-O—C(O)R4, -T-C(O)NR4R5, -T-NR4—C(O)R5, -T-NR4—SO2R5, —R6 and -T-R6 in which n, T, R4, R5 and R6 are as defined in the description, R3 represents an —R7 or —U—R11 group in which R7 represents hydrogen, alkyl, aryl, cycloalkyl or heterocycle, U represents a linear or branched alkylene chain and R11 is defined in the description, their optical isomers or their addition salts with a pharmaceutically acceptable acid or base, and their use as inhibitor of metalloproteinase and more specifically of metalloproteinase-12.
