74-41-9Relevant articles and documents
Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols
Annatelli, Mattia,Trapasso, Giacomo,Salaris, Claudio,Salata, Cristiano,Castellano, Sabrina,Aricò, Fabio
supporting information, p. 3459 - 3464 (2021/05/24)
N,N-dialkyl ethylamine moiety can be found in numerous scaffolds of macromolecules, catalysts, and especially pharmaceuticals. Common synthetic procedures for its incorporation in a substrate relies on the use of a nitrogen mustard gas or on multistep syntheses featuring chlorine hazardous/toxic chemistry. Reported herein is a one-pot synthetic approach for the easy introduction of aminoalkyl chain into different phenolic substrates through dialkyl carbonate (β-aminocarbonate) chemistry. This new direct alcohol substitution avoids the use of chlorine chemistry, and it is efficient on numerous pharmacophore scaffolds with good to quantitative yield. The cytotoxicity via MTT of the β-aminocarbonate, key intermediate of this synthetic approach, was also evaluated and compared with its alcohol precursor.
Synthesis of tetracyclic heterocompounds as selective estrogen receptor modulators. Part 2. Process improvement for scale-up of 2,5,8-substituted 11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta-[1,2-a]naphthalene derivatives
Li, Xun,Reuman, Michael,Russell, Ronald K.,Youells, Scott,Beish, Sandra,Hu, Zhiyong,Branum, Shawn,Jain, Nareshkumar,Sui, Zhihua
, p. 731 - 738 (2012/12/29)
An improved, reproducible nonchromatographic process for scale-up synthesis of 2,5,8-substituted 11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a] naphthalene derivatives as selective estrogen receptor modulators (SERMs) is described. The titled comp
Synthesis of tetracyclic heterocompounds as selective estrogen receptor modulators. Part 1. Process development for scale-up of 2,5,8-substituted 5,11 -dihydrochromeno[4,3-c]chromene derivatives
Li, Xun,Reuman, Michael,Russell, Ronald K.,Adams, Richard,Ma, Robert,Beish, Sandra,Branum, Shawn,Youells, Scott,Roberts, Jerry,Jain, Nareshkumar,Kanojia, Ramesh,Sui, Zhihua
, p. 414 - 421 (2012/12/31)
Unsymmetrical benzopyranobenzopyran compounds are novel selective estrogen receptor modulators (SERMs). A reproducible and nonchromatographic process was developed to prepare multihundred gram quantities of 5-(4-(2-(piperidin-1-yl) ethoxy)-phenyl)-5,11-di
Topologically Controlled Coulombic Interactions, a New Tool in the Developing of Novel Reactivity. Photochemical and Electrochemical Cleavage of Phenyl Alkyl Ethers
Marquet, Jorge,Cayon, Eduard,Martin, Xavier,Casado, Francisco,Gallardo, Iluminada,et al.
, p. 3814 - 3825 (2007/10/02)
The hypothesis that a specific placement of a positive charge would dramatically alter the behavior of a charged intermediate has been tested.Phenyl ethers substituted by electron-attracting groups do not undergo reductive fragmentation.However, related α-piperidino-ω-(4-substituted-phenoxy)alkanes give alkyl ether photocleavage when the linker between the redox centers is short, or the usual substitution-reduction photochemistry when it is long.Mechanistic experiments suggest that the photofragmentation process operates through space intramolecular electron transfer to the triplet aromatic chromophore and that a coplanar relative orientation of the alkyl ether bond and the phenyl ring is compulsory for the photofragmentation to be observed.Configuration interaction AM1 calculations justify the described facts, indicating that the fragmentation process is only operative when a Coulombic stabilization of a ?* intramolecular electron transfer excited state is produced.Electrochemical studies carried out with the corresponding quaternary salts (intermolecular generation of the phenyl ether radical anion) confirm the conclusions derived from the photochemical experiments.
Aminoindazole derivatives
-
, (2008/06/13)
A compound of the formula (I): STR1 wherein W1 and W2 each independently is a hydrogen atom or a STR2 group wherein Y is a n-C1-6 alkylene group or a n-C1-6 alkylene group having a C1-6 alkyl group substituent; and R1 and R2 each independently is a hydrogen atom or a C1-6 alkyl group, and STR3 group in STR4 group may form a saturated heterocyclic ring selected from the group consisting of morpholino, pyrrolidino, piperidino, homopiperidino and piperazino groups, and the saturated heterocyclic ring except the morpholino group may have at least one C1-4 alkyl group, hydroxyl group or halogen atom as a substituent; Z1 is a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, an amino group, a C1-3 alkyl group or a methoxy group; Z2 is a hydrogen atom or an amino group; when W1 and W2 are both hydrogen atoms, Z1 is a hydroxyl group or an iodine atom and Z2 is hydrogen atom, or Z1 and Z2 are both amino groups; when Z1 and Z2 are both hydrogen atoms, the STR5 group in either W1 or W2 is a morpholino group; when Z1 is a chlorine atom, a hydroxyl group, an iodine atom, a methyl group or a methoxy group, Z2 is a hydrogen atom; when Z1 is an amino group, Z2 is a hydrogen atom or an amino group; when Z1 is a methyl group, a methoxy group or an amino group, Z1 is in the 5-position; when Z1 is an iodine atom, Z1 is in the 5- or 7-position; and when Z1 and Z2 are both amino groups, Z1 and Z2 are in the 5- and 7-positions; and the physiologically acceptable acid addition salt thereof which compounds have pharmaceutical utility, e.g.: treating inflammation.
3-Aminoindazole derivatives
-
, (2008/06/13)
A compound of the formula (I): STR1 wherein W1 is a hydrogen atom or a STR2 group wherein Y is a C1-6 alkylene group or a C1-6 alkylene group having a C1-6 alkyl group substituent; and R1 and R2 each independently is a hydrogen atom or a C1-6 alkyl group and R1 and R2 may form a C4-6 heterocyclic ring or a nitrogen-containing C4-6 heterocyclic ring together with the adjacent nitrogen atom and the C4-6 heterocyclic rings may have at least one C1-6 alkyl group, hydroxyl group or halogen atom; W2 is a hydrogen atom or a STR3 group wherein Z is a C1-6 alkylene group or a C1-6 alkylene group having a C1-6 alkyl group substituent; and R3 and R4 each independently is a hydrogen atom or a C1-6 alkyl group and R3 and R4 may form a C4-6 heterocyclic ring or a nitrogen-containing C4-6 heterocyclic ring together with the adjacent nitrogen atom and the C4-6 heterocyclic rings may have at least one C1-6 alkyl group, hydroxyl group or halogen atom; when W1 is a hydrogen atom, W2 is the STR4 group; and when W2 is a hydrogen atom, W1 is the STR5 group; and the pharmaceutically acceptable acid addition salt thereof having antiinflammatory, analgesic and digestive tract ulcer suppressing activity.
