Regioselective synthesis of novel 3-alkoxy (phenyl) thiophosphorylamido-2-(per-O-acetylglycosyl-1'-imino)thiazolidine-4-one derivatives from O-alkyl N4-glycosyl(thiosemicarbazido)phosphonothioates.
A series of 3-alkoxy(phenyl)thiophosphorylamido-2-(per-O-acetylglycosyl-1'-imino)thiazolidine-4-one derivatives were prepared by the reaction of 1-alkoxy(phenyl)thiophosphoryl-4-(per-O-acetylglycosyl) thiosemicarbazides with ethyl bromoacetate. (1)H/(13)C HMBC measurements corroborated by X-ray crystallographic results revealed the exclusive regioselectivity of these ring closures toward the N-2 position of the thiosemicarbazide moiety. The bioactivity data of 3a-k suggest that the thiazolidine-4-one ring is critical for the herbicidal and fungicidal activities.
Li
Yu Xin
YX
State Key laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
Wang
Hao An
HA
Yang
Xiao Ping
XP
Cheng
Hai Ying
HY
Wang
Zhi Hong
ZH
Li
Yi Ming
YM
Li
Zheng Ming
ZM
Wang
Su Hua
SH
Yan
Dong Wen
DW
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects; D006540:Herbicides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012663:Semicarbazides / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000935:Antifungal Agents; D006540:Herbicides; D012663:Semicarbazides; D053778:Thiazolidines; C005151:thiosemicarbazide