104292-98-0Relevant articles and documents
Chemically-enabled synthesis of 1,2,3,4-tetrahydroisoquinolin-1-ones
Humphries, Paul S.,Balan, Gayatri,Bechle, Bruce M.,Conn, Edward L.,Dirico, Kenneth J.,Hui, Yu,Oliver, Robert M.,Southers, James A.,Yang, Xiaojing
, p. 2140 - 2143 (2009)
We have developed a number of efficient protocols for the facile synthesis of 1,2,3,4-tetrahydroisoquinolin-1-ones. This synthetic methodology allowed concise and efficient exploration of the SAR in all areas of the molecule. A number of these methods pro
Ni-Catalyzed Reductive C-O Bond Arylation of Oxalates Derived from α-Hydroxy Esters with Aryl Halides
Gao, Mengyu,Sun, Deli,Gong, Hegui
supporting information, p. 1645 - 1648 (2019/03/11)
A Ni-catalyzed reductive cross-coupling of α-hydroxycarbonyl compounds modified with oxalyl groups and aryl halides has been developed that furnishes α-aryl esters under mild conditions and tolerates a variety of functionalized aryl halides bearing electron-withdrawing and -donating groups. This work highlights C-O bond fragmentation on secondary alkyl carbon centers that generates α-carbonyl radicals.
2-Hydroxyisoquinoline-1,3(2H,4H)-diones as inhibitors of HIV-1 integrase and reverse transcriptase RNase H domain: Influence of the alkylation of position 4
Billamboz, Muriel,Bailly, Fabrice,Lion, Cedric,Calmels, Christina,Andreola, Marie-Line,Witvrouw, Myriam,Christ, Frauke,Debyser, Zeger,De Luca, Laura,Chimirri, Alba,Cotelle, Philippe
experimental part, p. 535 - 546 (2011/03/19)
We report herein the synthesis of a series of fifteen 2- hydroxyisoquinoline-1,3(2H,4H)-dione derivatives. Alkyl and arylalkyl groups were introduced on position 4 of the basis scaffold. All the compounds presented poor inhibitory properties against HIV-1 reverse transcriptase ribonuclease H (RNase H). Four compounds inhibited HIV-1 integrase at a low micromolar level. A docking study using the later crystallographic data available for PFV integrase allowed us to explain the slightly improved integrase inhibitory activities of 4-pentyl and 4-(3-phenylpropyl)-2-hydroxyisoquinoline-1,3(2H,4H)-diones, when compared to the basis scaffold. Physicochemical studies were consistent with 1:1 and 1:2 (metal/ligand) stoichiometries of the magnesium complexes in solution. Unfortunately all tested compounds exhibited high cellular cytotoxicity in cell culture which limited their applications as antiviral agents. However these identified integrase inhibitors provide a very good basis for the development of new hits.
Ni-catalyzed activation of α-chloroesters: a simple method for the synthesis of α-arylesters and β-hydroxyesters
Durandetti, Muriel,Gosmini, Corinne,Périchon, Jacques
, p. 1146 - 1153 (2007/10/03)
Coupling reactions of α-chloroesters with aryl halides (α-arylation) or carbonyl compounds (Reformatsky) using nickel catalyst allow, under mild conditions, the preparation of various functionalized aryl propionic acid derivatives or β-hydroxyesters. In the synthesis of aryl propionic acid derivatives, the process is efficient with aryl halides bearing either electron-withdrawing or electron-donating groups.
An Improved Synthesis of Naphthoate Precursors to Olivin
Roush, William R.,Murphy, Megan
, p. 6622 - 6629 (2007/10/02)
An improved synthesis of olivin synthetic intermediate 3 is described.The synthesis involves the Horner-Wadsworth-Emmons coupling of 14 and 16, the diastereoselective vinylcuprate addition to enone 20, and the condensation of isocoumarin 25 and methyl acetate.A parallel sequence starting from allyl ether 26 has provided naphthoate 35 that is suitably differentiated for glycosylation studies.
A Synthesis of Polycyclic Aromatic Compounds by the Ca(OAc)2-Induced Aromatization of Polyoxoalkanedioates Generated from Diesters and Acetoacetate Dianion
Yamaguchi, Masahiko,Hasebe, Koichi,Higashi, Hirofumi,Uchida, Minoru,Irie, Akemi,Minami, Toru
, p. 1611 - 1623 (2007/10/02)
The dual-Claisen condensation of diesters with acetoacetate dianion generated tetraoxoalkanedioates, whose aromatization by Ca(OAc)2-promoted intramolecular condensation constructed two carbocyclic rings containing phenol part.The reactions converted glutarates to bicyclic phenols and homophthalates to 1,9-dihydroxyanthracenes.The latters were air-oxidized to anthraquinones in the presence of K2CO3.The regiochemistry of the arene synthesis was studied.As the products of this synthesis also were glutarates, further extension of the aromatic ring system was carried out.Pentacenequinones were synthesized from anthracenes, while anthraquinones gave naphthacenequinones.The reactions are related to the biosynthesis of polycyclic aromatic compounds, and arenes obtained are useful intermediates in the natural products synthesis.A formal synthesis of aklavinone was achieved.
Facile and Efficient Syntheses of Carboxylic Anhydrides and Amides Using (Trimethylsilyl)ethoxyacetylene
Kita, Yasuyuki,Akai, Shuji,Ajimura, Naomi,Yoshigi, Mayumi,Tsugoshi, Teruhisa,et al.
, p. 4150 - 4158 (2007/10/02)
(Trimethylsilyl)ethoxyacetylene, a stable and easy-handling reagent, serves as an excellent dehydrating agent for the synthesis of carboxylic anhydrides and amides from the corresponding carboxylic acids.By means of this reagent, various types of acid-sensitive carboxylic anhydrides and amides were obtained almost in quantative yields.Twenty-two examples of carboxylic anhydrides and 12 examples of amides were presented.
