177944-16-0Relevant academic research and scientific papers
3-(5-METHOXY-1-OXOISOINDOLIN-2-YL)PIPERIDINE-2,6-DIONE DERIVATIVES AND USES THEREOF
-
Page/Page column 343, (2021/06/26)
The present disclosure relates to compounds of formula (I') and pharmaceutical compositions and their use in reducing Widely Interspaced Zinc Finger Motifs (WIZ) expression levels, or inducing fetal hemoglobin (HbF) expression, and in the treatment of inherited blood disorders (e.g., hemoglobinopathies, e.g., beta-hemoglobinopathies), such as sickle cell disease and beta-thalassemia.
Preparation method of griseine key intermediate
-
Paragraph 0026-0032, (2021/09/29)
The preparation method comprises S1, sequentially adding 4A molecular sieve, acetonitrile and a compound shown in structural formula 1 into acrylic acid, performing a Diels - Alder reaction, and obtaining an intermediate product. TLC A neutralization reag
A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of 4-Chloropiperidines from Homoallylic Amines
Ebule, Rene,Mudshinge, Sagar,Nantz, Michael H.,Mashuta, Mark S.,Hammond, Gerald B.,Xu, Bo
, p. 3249 - 3259 (2019/03/20)
We report that HCl·DMPU induces the formation of (thiomethyl)methyl carbenium ion from DMSO under mild conditions. Homoallylic amines react with this electrophile to generate 4-chloropiperidines in good yields. The method applies to both aromatic and aliphatic amines. The use of HCl·DMPU as both non-nucleophilic base and chloride source constitutes an environmentally benign alternative for piperidine formation. The reaction has a broad substrate scope, and the conditions offer good chemical yields with high functional group tolerance and scalability.
Dimethylamine adducts of allylic triorganoboranes as effective reagents for Petasis-type homoallylation of primary amines with formaldehyde
Kuznetsov, Nikolai Yu.,Tikhov, Rabdan M.,Strelkova, Tatiana V.,Bubnov, Yuri N.
supporting information, p. 7115 - 7119 (2018/10/23)
Dimethylamine adducts of triallyl-, triprenyl- and trans-cinnamyl(dipropyl)borane are effective reagents for mild homoallylation of primary amines with aqueous formaldehyde in MeOH without an inert atmosphere. A new concept is proposed for the explanation of the high stability of allylborane-amine adducts in aqueous MeOH.
(Indazol-4-YL) Hexahydropyrrolopyrrolones and Methods of Use
-
Paragraph 0294, (2016/10/04)
Compounds of formula (I) and pharmaceutically acceptable salts, esters, amides, or radiolabelled forms thereof, wherein GAr, L1, Z1 and Z2 are as defined in the specification, are useful in treating conditions or disorders prevented by or ameliorated by voltage-gated sodium channels, e.g., Nav 1.7 and/or Nav 1.8. Methods for making the compounds are disclosed. Also disclosed are pharmaceutical compositions of compounds of formula (I), and methods for using such compounds and compositions.
Asymmetric syntheses of (-)-3-epi-fagomine, (2 R,3 S,4 R)-dihydroxypipecolic acid, and several polyhydroxylated homopipecolic acids
Csatayov, Kristna,Davies, Stephen G.,Fletcher, Ai M.,Ford, J. Gair,Klauber, David J.,Roberts, Paul M.,Thomson, James E.
, p. 10932 - 10944 (2015/01/09)
A range of enantiopure polyhydroxylated piperidines, including (2R,3S,4R)-dihydroxypipecolic acid, (-)-3-epi-fagomine, (2S,3S,4R)-dihydroxyhomopipecolic acid, (2S,3R,4R)-dihydroxyhomopipecolic acid, and two trihydroxy-substituted homopipecolic acids, have been prepared using diastereoselective olefinic oxidations of a range of enantiopure tetrahydropyridines as the key step. The requisite substrates were readily prepared from tert-butyl sorbate using our diastereoselective hydroamination or aminohydroxylation protocols followed by ring-closing metathesis. After diastereoselective olefinic oxidation of the resultant enantiopure tetrahydropyridines and deprotection, enantiopure polyhydroxylated piperidines were isolated as single diastereoisomers (>99:1 dr) in good overall yield.
Asymmetric synthesis of polyhydroxylated pyrrolizidines via transannular iodoamination with concomitant N-debenzylation
Brock, E. Anne,Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Thomson, James E.
body text, p. 1594 - 1597 (2011/05/03)
The doubly diastereoselective "matched" conjugate addition of lithium (R)-N-but-3-enyl-N-(α-methyl-p-methoxybenzyl)amide to tert-butyl (4S,5R,E)-4,5-O-isopropylidene-2,7-dienoate (derived from d-ribose in 3 steps) and in situ enolate oxidation with (-)-camphorsulfonyloxaziridine was followed by ring-closing metathesis with Grubbs I to give a hexahydroazocine scaffold. Subsequent treatment with I2 resulted in transannular iodoamination accompanied by loss of the α-methyl-p-methoxybenzyl group to give the corresponding pyrrolizidine scaffold as a single diastereoisomer upon direct crystallization from the crude reaction mixture. Further functional group manipulations enabled the preparation of (-)-7a-epi-hyacinthacine A1.
Cyclization of zincated α-N-homoallylamino nitriles: A new entry to enantiopure 2,3-methanopyrrolidines
Ouizem, Sabrina,Cheramy, Sandrine,Botuha, Candice,Chemla, Fabrice,Ferreira, Franck,Perez-Luna, Alejandro
supporting information; experimental part, p. 12668 - 12677 (2011/02/22)
Stereoselective cyclization of zincated α-N-homoallylamino nitriles has been developed. Following treatment with lithium diisopropylamide (LDA) and transmetalation with zinc bromide, α-N-(1-phenylethyl)-N-homoallylamino nitriles lead to 2,3-methanopyrroli
Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition
Davies, Stephen G.,Fletcher, Ai M.,Roberts, Paul M.,Smith, Andrew D.
body text, p. 10192 - 10213 (2010/02/28)
Conjugate addition of lithium (R)-N-allyl-N-(α-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(α-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant β-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed to a range of piperidine alkaloids of the Sedum family, and the corresponding five-, seven- and eight-membered ring homologues.
Synthetic studies toward paraherquamides E and F and related 13C-labeled putative biosynthetic intermediates: stereocontrolled synthesis of the α-alkyl-β-methylproline ring system
Sommer, Konrad,Williams, Robert M.
, p. 7106 - 7111 (2008/12/20)
A substituted 2R-allyl-3S-methylproline ethyl ester suitable for elaboration to paraherquamides E, F and related 13C-labeled putative biosynthesis intermediates have been prepared efficiently in six steps and?24% overall yield. The key steps are a 5-exo-trig cyclization of a zinc enolate on an unactivated alkene and a stereocontrolled alkylation of the enolate formed from 3S-methyl-pyrrolidine-1,2R-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester.
