136607-65-3Relevant academic research and scientific papers
Preparation of new nitrogen-bridged heterocycles. 46. Selective formation of 4(1H)-8,8a-dihydro-1,4-thiazino[3,4,5-cd]indolizinone and (E)- 3-(1,3-oxathiol-2-ylidene)-2(3H)-indolizinone derivatives
Kakehi, Akikazu,Ito, Suketaka,Suga, Hiroyuki,Kobayashi, Toshiyuki,Hatanaka, Susumu
, p. 1866 - 1871 (1998)
The reactions of (Z)-3-[mercapto(methylthio)methylene]-2(3H)- indolizinones with bromoacetonitrile and bromoacetates in the presence of a base gave the corresponding 4(1H)-8,8a-dihydro-1,4-thiazino[3,4,5- cd]indolizinone derivatives, but similar treatment of the same compounds with some phenacyl bromides provided a quite different type of product, (E)-3-(5- aryl-1,3-oxathiol-2-ylidene)-2(3h)-indolizinones, in 12-74% yield with the evolution of methanethiol. Interestingly, the reactions of (Z)-3- [mercapto(phenacylthio)methylene]-2(3H)-indolizinones and iodomethane in the presence of a base did not afford the expected (Z)-3-(5-aryl-1,3-oxathiol-2- ylidene)-2(3H)-indolizinones, but gave only the same (E)-isomers in 22-53% yields. The stereochemistry about the C3-C2' double bond in these 3-(5-aryl- 1,3-oxathiol-2-ylidene)-2(3H)-indolizinones was determined to be (E) by X- ray analysis.
A new synthetic approach to some functionalized cycl[3.2.2]azine derivatives
Muranaka, Hideyuki,Kakehi, Akikazu,Suga, Hiroyuki,Itoh, Kennosuke
experimental part, p. 1251 - 1266 (2011/05/05)
Dehydrogenation of some ethyl 4-oxo-1H-8,8a-dihydro-1,4-thiazino[3,4,5-cd] indolizine-1-carboxylates with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) were examined. No simply dehydrogenated products such as 4-oxo-1H-and 4-oxo-8H-1,4-thiazino[3,4,5-cd]
