文献类型：期刊文献

英文题名：Synthesis of ursane-derived isothiocyanates and study of their reactions with series of amines and ammonia

作者：Popov, Sergey A.[1,3] Qi, Zhiwen[2] Wang, Chengzhang[2] Shults, Elvira E.[1]

第一作者：Popov, Sergey A.

通信作者：Popov, SA[1]

机构：[1]Novosibirsk Inst Organ Chem, Novosibirsk, Russia;[2]Chinese Acad Forestry, Inst Chem Ind Forest Prod, Nanjing, Peoples R China;[3]Novosibirsk Inst Organ Chem, Acad Lavrentyev Ave 9, Novosibirsk 630090, Russia

年份：0

外文期刊名：JOURNAL OF SULFUR CHEMISTRY

收录：;Scopus(收录号：2-s2.0-85150991786);WOS:【SCI-EXPANDED(收录号:WOS:000951856100001)】；

基金：This work was supported by state assignment of Ministry of Science and Education of the Russian Federation (project 1021051503128-9-1.4.1). Analytical and spectroscopic studies were performed at the Chemical Service collective Center of SB RAS~.

语种：英文

外文关键词：Ursane hybrids; isothiocyanate; 4; 5-dihydrothiazol-2-amine; 1; 2; 3-triazole; thiourea derivative

摘要：Based on ursolic acid, 3 compounds with isothiocyanate groups located at different distances from C-17 of the triterpenoid core have been synthesized through ursane-derived primary amines. To obtain terpene hybrids with thioureas and N,S-containing heterocycles, series of amines and ammonia were reacted with novel isothiocyanates. In the reactions with propargylamine, 3 triterpenoid hybrids with 4,5-dihydrothiazol-2-yl-amine have been selectively obtained in 81%-91% yields. Isothiocyanates containing several bonds between the -CNS group and the triterpenoid backbone reacted with (1-aryl-1H-1,2,3-triazole-4-yl)methanamines, as well as with ammonia, to form thiourea derivatives (78%-94%). The nor-compound with a -CNS group at C-17 of the triterpenoid was the least reactive due to deactivation by a donor terpene branched substituent and reacted readily only with sufficiently strong nucleophiles, such as primary and secondary aliphatic amines. The reaction of the nor-derivative of isothiocyanate 7 with ammonia at elevated temperature led to the unexpected formation of 3 beta-acetoxy-28-norurs-12-en-17-yl-amine, the precursor of isothiocyanate, as the main product (82%).