108046-33-9Relevant articles and documents
One-pot synthesis of cyclic enecarbamates from lactam carbamates
Yu, Jurong,Truc, Vu,Riebel, Peter,Hierl, Elizabeth,Mudryk, Boguslaw
, p. 4011 - 4013 (2005)
A general, practical and efficient one-pot synthesis of cyclic enecarbamates is described. The protocol proceeds via reduction of lactam carbamate with Super-Hydride, followed by in situ dehydration with trifluoroacetic anhydride (TFAA) and diisopropylethylamine (DIPEA).
NEW ROUTES TO NITROGEN HETEROCYCLES THROUGH INTRAMOLECULAR AMIDOCARBONYLATON OF ALKENAMIDES CATALYZED BY RHODIUM COMPLEXES
Ojima, Iwao,Korda, Anna
, p. 6283 - 6286 (1989)
Intramolecular amidocarbonylation of 3-butenamide catalyzed by a rhodium complex with excess PPh3 gives 3,4-dihydro-2-pyridone selectively, whereas the same reaction using P(OPh)3 affords a unique heterodimer in excellent yield.The reaction of 4-pentenamide gives 4-methyl-3,4-dihydro-2-pyridone exclusively regardless of the structure of rhodium catalysts.
?-C(sp2)-H alkylation of enamides using xanthate chemistry
Bertho, Sylvain,Dondasse, Isma?l,Retailleau, Pascal,Nicolas, Cyril,Gillaizeau, Isabelle
, p. 7129 - 7141 (2020)
Access to the ?-amino-?,?-unsaturated acyl scaffold was established by applying xanthate chemistry to enamides. This original ?-C(sp2)-H alkylation is regioselective and exhibits broad substrate scope and good functional group tolerance. The la
The Reactivity of Enantiopure (S)-6-Oxopipecolic Acid and Corresponding Pyridoisoquinolines Under Acidic Conditions
?afá?, Peter,Marchalín, ?tefan,Balónová, Barbora,?oral, Michal,Moncol, Ján,Ghinet, Alina,Rigo, Beno?t,Da?ch, Adam
, p. 5499 - 5511 (2018)
Enantiopure N-benzyl 6-oxopipecolic acid, obtained from (S)-2-aminoadipic acid, was evaluated under π-cationic cyclization conditions. If the combination of SOCl2/AlCl3 seems to be superior in terms of the reaction yields, use of PPA
Synthesis of β-Diamine Building Blocks by Photocatalytic Hydroamination of Enecarbamates with Amines, Ammonia and N?H Heterocycles
Francis, Daniel,Nelson, Adam,Marsden, Stephen P.
supporting information, p. 14861 - 14865 (2020/10/12)
3-Amino-substituted saturated nitrogen heterocycles are an important subclass of β-diamines, appearing in a number of clinical agents. Herein, we report a unified approach to these products based upon the regioselective photoredox-mediated hydroamination of enecarbamates. The amine coupling partner can encompass diverse amine types under a single set of reaction conditions, including primary alkyl amines, ammonia, aryl and heteroaryl amines, and N?H heterocycles. The method enables the synthesis of a wide range of pharmaceutically relevant building blocks.
One-pot synthesis of pyrrolidino- and piperidinoquinolinones by three-component aza-Diels-Alder reactions of in situ generated N-arylimines and cyclic enamides
Zhang, Wei,Zhang, Wenxue,Dai, Yisi,Wang, Xuerui
, p. 6122 - 6126 (2011/12/01)
An efficient synthesis of hexahydropyrrolo[3,2-c]quinolin-2-ones and hexahydropyridino[3,2-c]quinolin-2-ones has been developed in moderate to high yields by one-pot two-step aza-Diels-Alder reactions of N-arylimines, formed in situ from anilines and benz
Synthesis of 2-azabicyclo[4.1.0]heptanes through stereoselective cyclopropanation reactions
Suarez Del Villar, Irene,Gradillas, Ana,Perez-Castells, Javier
, p. 5850 - 5862 (2011/03/17)
Unsaturated δ-lactams are cyclopropanated with the aid of diazo compound decomposition catalysed by metal complexes. A study of the reaction conditions, stereochemical outcome and group protection is reported. The resulting bicyclic products are related to bioactive compounds. Transformation into thiolactams facilitates the separation of the different isomers obtained and the removal of the protecting group. The cyclopropanation reaction works with diverse diazo compounds. Unsaturated δ-lactams are cyclopropanated with the aid of diazo compound decomposition catalysed by metal complexes. A study of the reaction conditions, stereochemical outcome and group protection isreported. Transformation into thiolactams assists in separation of the different isomers obtained and removal of the protecting group.
Unsaturated lactams: New inputs for povarov-type multicomponent reactions
Vicente-Garcia, Esther,Catti, Federica,Ramon, Rosario,Lavilla, Rodolfo
supporting information; body text, p. 860 - 863 (2010/04/29)
Unsaturated lactams with endo- or exocyclic C-C double bonds constitute a set of reactive inputs that serve as the electron-rich olefin component in Povarov reactions. These substrates afford the multicomponent adducts in convenient yields and offer a wid
Design and synthesis of all diastereomers of cyclic pseudo-dipeptides as mimics of cyclic CXCR4 pentapeptide antagonists
Cluzeau, Jerome,Oishi, Shinya,Ohno, Hiroaki,Wang, Zixuan,Evans, Barry,Peiper, Stephen C.,Fujii, Nobutaka
, p. 1915 - 1923 (2008/02/10)
The four diastereomers of 2,5-bis[(3-guanidino)propyl]-1-[3-(4- hydroxyphenyl)propionyl]-7-(2-naphthylacetyl)-1,4,7-triazacycloundec-9-en-3-one (54-57) and of 2,5-bis[(3-guanidino)propyl]-1-(4-hydroxyphenylacetyl)-7-(2- naphthylacetyl)-1,4,7-triazacycloundec-9-en-3-one (58-61) were synthesized by a divergent methodology from l- and d-glutamic acids. The 11-membered ring core was made by ring closing metathesis of linear bis(allylamines), and the guanidyl functions were introduced by a simultaneous double Mitsunobu reaction using bis(Boc)guanidine. These compounds were designed to mimic cyclic pentapeptide FC131 (c[Gly-d-Tyr-Arg-Arg-Nal]). The Royal Society of Chemistry.
Facile carbamoylation of 3,4-dihydropyridin-2-one with N-chlorosulfonyl isocyanate
Sa?ański, Piotr,Young, Kwan Ko,Lee, Kee-In
, p. 46 - 48 (2007/10/03)
3,4-Dihydro-2-pyridone-5-carboxylic acid amides were prepared by carbamoylation at the C-5 position of 3,4-dihydropyridin-2-one with N-chlorosulfonyl isocyanate.
