39077-95-7Relevant academic research and scientific papers
Electrochemical metal- And oxidant-free synthesis of S-thiocarbamates
Malviya, Bhanwar Kumar,Sharma, Siddharth,Verma, Ved Prakash
, p. 9491 - 9500 (2021/11/17)
An expeditious synthetic strategy to access functionalized S-thiocarbamates was developed in good to excellent yields and with high current efficiencies. Readily available isocyanides and thiols were used as the starting materials under simple metal- and oxidant-free reaction conditions avoiding an inert atmosphere. The practical application of the present methodology was achieved by electrochemical synthesis of the herbicides prosulfocarb and pebulate. Furthermore, continuous electrochemical flow conditions using a graphite/Pt flow cell were used to obtain S-thiocarbamate compounds on a gram scale within a residence time of 35 min. This journal is
Aromatic Allylsulfenylation with in Situ Generated Allylic Thiols under the Heck Conditions
Harayama, Hiroto,Nagahama, Takayuki,Kozera, Toyohiro,Kimura, Masanari,Fugami, Keigo,Tanaka, Shuji,Tamaru, Yoshinao
, p. 445 - 456 (2007/10/03)
A wide structural variety of S-allylic thiocarbamates 2 can be prepared in good yields by the rearrangement of O-allylic thiocarbamates 1 under three different conditions: thermal activation (neat, 120-150°C), palladium(0) (25-65 °C), and palladium(II) catalysis (25-65°C). Of the two possible regioisomers of unsymmetrical S-allylic thiocarbamates 2, those of higher thermodynamic stability can be prepared in high purity under either thermal activation or palladium(0) catalysis. Although the thermodynamically less stable regioisomers of 2 are, in general, hard to be prepared in high purity, some of them (e.g., 2d and 2h′) can be obtained with an exclusive or high selectivity by the catalysis of palladium(II). The stereoisomeric pair of 2j and 2j′ can be prepared selectively by the palladium(0)-catalyzed rearrangement of 1j and 1k, respectively. These reactions proceed with retention of configuration at the allylic stereocenters, S-Allylic (2) and S-alkyl thiocarbamates (7) undergo fragmentation to generate thiolates in the presence of inorganic bases (e.g., K2CO3, K2CO3·-Et4N+I-) by heating in an aprotic solvent; the thus-formed thiolates react with aromatic iodides and vinyl bromides in the presence of palladium(0) complexes to furnish aryl and vinyl sulfides, respectively. A wide variety of aryl sulfides can be prepared in good yields irrespective of the kind of substituents and their substitution positions (o-, m-, p-) under conditions B [Pd(OAc)2, PPh3, K2CO3·Et4N+I-, dioxane, 100°C]. Under conditions E [Pd(OAc)2, PPh3, Cs2CO3, dioxane, 100°C], better yields result specifically for the sulfenylation of aromatic iodides bearing substituents having large Hammett σ constants.
Latent alkyl isocyanates as inhibitors of aldehyde dehydrogenase in vivo
Nagasawa,Elberling,Goon,Shirota
, p. 4222 - 4226 (2007/10/02)
On the basis of our previous observation that N1-alkyl substituted chlorpropamide derivatives when administered to rats nonenzymatically eliminated n-propyl isocyanate, a known inhibitor of aldehyde dehydrogenase (AlDH), we have synthesized oth
