3422-75-1Relevant articles and documents
1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: An Efficient Synthesis of 2-Quinolinones via β-Keto Amides
Vala, Anand,Parmar, Nirali,Soni, Jigar Y.,Kotturi, Sharadsrikar,Guduru, Ramakrishna
supporting information, p. 2080 - 2084 (2021/10/07)
Under thermal conditions, 1,4,2-dioxazol-5-ones are known to undergo decarboxylation followed by Lossen's rearrangement to yield isocyanates. Described herein is the in situ trapping of the resulting isocyanates with carbon nucleophiles to synthesize β-keto amides. Furthermore, a general and mild method for the conversion of the resulting β-keto amides into quinolin-2-ones is reported.
One-pot synthesis of 3-hydroxyquinolin-2(1 H)-ones from N-phenylacetoacetamide via PhI(OCOCF3)2-mediated α-hydroxylation and H2SO4-promoted intramolecular cyclization
Yuan, Yucheng,Yang, Rui,Zhang-Negrerie, Daisy,Wang, Junwei,Du, Yunfei,Zhao, Kang
, p. 5385 - 5392 (2013/07/26)
A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF 3)2-mediated α-hydroxylation and a H 2SO4-promoted intramolecular condensation. The hydroxyl group in the generated α-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.
A highly enantioselective Darzens reaction between diazoacetamides and aldehydes catalyzed by a (+)-pinanediol-Ti(OiPr)4 system
Liu, Gang,Zhang, Daming,Li, Jian,Xu, Guangyang,Sun, Jiangtao
, p. 900 - 904 (2013/02/25)
A highly efficient enantioselective Darzens reaction of aldehydes with diazoacetamides catalyzed by a (+)-pinanediol-Ti(OiPr)4 system has been developed. The cis-glycidic amides were obtained in high yields and with moderate to excellent enantioselectivity (up to 99%).
Highly enantioselective epoxidation catalyzed by cinchona thioureas: Synthesis of functionalized terminal epoxides bearing a quaternary stereogenic center
Russo, Alessio,Galdi, Gerardina,Croce, Gianluca,Lattanzi, Alessandra
supporting information; experimental part, p. 6152 - 6157 (2012/06/30)
A brilliant debut! Cinchona thioureas have been reported for the first time as catalysts in the area of asymmetric oxidations. They efficiently promote an unprecedented highly enantioselective epoxidation of deactivated 1,1-disubstituted alkenes to terminal epoxides containing a quaternary stereogenic center (see scheme). Copyright
Enamines in solid-phase: Synthesis and reactivity towards electrophiles
Aznar, Fernando,Valdés, Carlos,Cabal, María-Paz
, p. 5683 - 5687 (2007/10/03)
Enamines are synthesized in solid-phase by amination of terminal, acetylenes with a secondary amine attached to Wang resin in a process catalyzed by mercury (II) acetate. The enamines obtained react with electrophiles such as isocyanates and nitroolefins to give rise to the expected addition products, which can be released from the resin by hydrolysis of the enamine under mild acidic conditions. (C) 2000 Elsevier Science Ltd.
REACTION OF 2,2-DIMETHYL-6-ARYL-1,3-DIOXIN-4-ONES WITH AROMATIC AMINES AND o-PHENYLENEDIAMINE
Andreichikov, Yu. S.,Gein, V. L.,Kozlov, A. P.,Vinokurova, O. V.
, p. 189 - 194 (2007/10/02)
N-Arylaroylacetamides and 4-aryl-1,5-benzodiazepin-4-ones were obtained by the thermolysis of 2,2-dimethyl-6-aryl-1,3-dioxin-4-ones in the presence of aromatic amines and o-phenylenediamine respectively.Investigetion of the reaction kinetics showed that the controlling stage is the generation of the aroylketenes, which takes place by a concerted -retrocycloaddition mechanism.
