- Transition metal free synthesis of multifunctional thiomethylated-benzenes from aryl/heteroaryl/cyclopropyl methyl ketones
-
A base-promoted strategic synthesis of various functionalized thiomethylated-benzenes has been established from aryl/heteroaryl/cyclopropyl methyl ketone. We can directly access the thiomethylated-benzene nucleus embedded with diverse functional group by
- Panwar, Rahul,Althagafi, Ismail,Shally,Shaw, Ranjay,Elagamy, Amr,Shah, Chandan,Yadav, Pratik,Pratap, Ramendra
-
-
- Synthesis of 2,4,5-Trisubstituted Oxazoles with Complementary Regioselectivity from α-Oxoketene Dithioacetals and β-(Methylthio)-β-(het)aryl-2-propenones
-
An efficient protocol for the synthesis of 2,5-substituted 4-acyloxazoles and the related 2,4-substituted 5-acyloxazoles with complementary regioselectivity from the corresponding α-oxoketene dithioacetals or β-(het)aryl/(methylthio)enone precursors has been reported. In the first protocol, the α-oxoketene dithioacetals or β-(methylthio)enones were converted to the corresponding α-bromo-β-(methylthio)enones followed by copper catalyzed inter/intramolecular annulation of these intermediates with various primary amides affording 2-(het)aryl/alkyl-4-(het)aroyl-5-(methylthio)/(het)aryloxazoles via concomitant formation of the C4-N and C5-O bond via enamide intermediates. In the second approach, the starting α-oxoketene dithioacetals or β-(methylthio)-β-(het)arylenones were subjected to base induced conjugate addition-elimination with various primary amides to furnish β-aroylenamides, which, on subsequent iodine catalyzed intramolecular oxidative C-H functionalization/C-O bond formation, afforded the corresponding regioisomeric 2-(het)aryl/alkyl-4-(methylthio)/(het)aryl-5-(het)aroyloxazoles in excellent yields. The methodology has also been extended for the synthesis of regioisomeric 4- or 5-aminooxazoles and 4- or 5-(n-butyl)oxazoles from the corresponding 4- or 5-(methylthio)oxazoles.
- Kumar, Siripuram Vijay,Acharya, Anand,Ila, Hiriyakkanavar
-
p. 6607 - 6622
(2018/05/23)
-
- Bronsted acid catalyzed PhSe transfer versus radical aryl transfer: Linear codimerization of styrenes and internal olefins
-
Bronsted acid p-TsOH·H2O-catalyzed hydrovinylation of styrenes with internal olefins α-oxo ketene dithioacetals was efficiently achieved in the presence of N-phenylselenophthalimide (N-PSP), regioselectively affording Markovnikov phenylselenati
- Wu, Ping,Wang, Liandi,Wu, Kaikai,Yu, Zhengkun
-
supporting information
p. 868 - 871
(2015/03/30)
-
- Base mediated synthesis of α-aminated aroyl/acetylnaphthalenes through [4+2] annulations
-
We have developed a base promoted simple, efficient and alternative approach for the synthesis of 4-amino-3-aroyl//heteroaroyl/acetyl-2-methylsulfanyl-naphthalene-1-carbonitriles by reaction of easily accessible 3,3-bis(methylthio)-1-aryl/heteroaryl/acety
- Singh, Surjeet,Althagafi, Ismail,Yadav, Pratik,Panwar, Rahul,Kumar, Abhinav,Pratap, Ramendra
-
p. 8879 - 8884
(2015/03/05)
-
- A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from α-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations
-
A convenient base-mediated strategy to synthesize 3-aryol-4-methyl (or benzyl)-2-methylthio furans 2 (trisubstituted furans) has been developed through the domino coupling/annulations between available α-oxo ketene dithioacetals 1 and propargyl alcohols.
- Yang, Xiaobing,Hu, Fangzhong,Di, Hongjing,Cheng, Xinxin,Li, Dan,Kan, Xiaoli,Zou, Xiaomao,Zhang, Qichun
-
supporting information
p. 8947 - 8951
(2014/12/11)
-
- One-pot straightforward approach to 2,3-disubstituted benzo/naphtho[b] furans via domino annulation of α-oxoketene dithioacetals and 1,4-benzo/naphthoquinone mediated by AlCl3 at room temperature
-
A versatile and convenient one-pot direct approach to 2,3-disubstituted benzo/naphtho[b]furans via domino annulation of α-oxoketene dithioacetals and 1,4-benzo/naphthoquinone has been achieved in the presence of aluminium chloride at room temperature. Thi
- Verma, Girijesh Kumar,Verma, Rajiv Kumar,Shukla, Gaurav,Anugula, Nagaraju,Srivastava, Abhijeet,Singh, Maya Shankar
-
p. 6612 - 6619
(2013/07/26)
-
- A Practical Synthetic Method for β-Ketosters from Ketones
-
A practical, simple, one-pot synthesis of β-ketoesters (3) from ketones (1) via bis(methylthio)ketene acetals (4) was achieved. Keywords---β-ketoester; bis(methylthio)ketene acetals; C-alkoxycarbonylation; ketone; carbon disulfide
- Tomozane, Hideo,Takeuchi, Yasuo,Yamato, Masatoshi
-
p. 401 - 404
(2007/10/02)
-
- Synthesis of 2,6-Disubstituted Pyridines, Polypyridinyls, and Annulated Pyridines
-
1,5-Enediones containing a variety of substituents in the 1,5-positions are formed in good yields by the reaction of methyl ketone enolates, generated with potassium tert-butoxide, with α-oxoketene dithioacetals, the latter being prepared from alkyl, cycloalkyl, aryl, or heteryl methyl ketones, NaH, CS2, and CH3I.Ring closure of the 1,5-enediones with NH4OAc gave 2,6-disubstituted 4-(methylthio)pyridines in good to excellent yields.This procedure is particularly suited for the synthesis of 2,6-diheterylpyridines and provides a simple synthesis of terpyridinyl and other oligopyridines.The methylthio groups in the α-oxoketene dithioacetals may be oxidized to the mono- and disulfoxides with m-chloroperbenzoic acid, but with excess peracid, in addition to oxidation to the disulfone, epoxidation of the double bond also occurs.The pyridine 4-methylthio substituent may also be oxidized to the sulfoxide and to the sulfone, and the latter may be displaced with cyanide ion to form the corresponding 4-carbonitrile.
- Potts, Kevin T.,Cipullo, Michael J.,Ralli, Philip,Theodoridis, George
-
p. 3027 - 3038
(2007/10/02)
-