Syntheses of new mesoionrc compounds = 새로운메소이온 화합물의 합성

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New mesoionic compounds were synthesized from the reaction of chlorosulfonly isocynate (CSI) or pentachlorophenyl N-chlorosulfonylcarbamate (PCPCSC) with amidine compounds in the presence of ethyldiisopropylamine. CSI or PCPCSC reacted with 2-benzylaminopyridine producing intermediate which was cyclized to afford mesoionic 1-benzylpyrido[1,2-b][1,2,4,6]thiatriazine-2,4,4-trioxide in the presence of tertiary amine base at room temperature. 2-Alkylaminothiazoles afforded mesoionic 1-alkylthiazolo[2,3-c][1,2,4,6]thiatriazine-2,4,4-trioxides with CSI and mesoionic 1-alkylthiazolo[3,2-b]-[1,2,4,6]thiatriazine-2,4,4-trioxideswith PCPCSC in the presence of a tertiary amine base in chloroform at room temperature, respectively. 2-Alkylaminobenzothiazoles frequently gave mixture of mesoionic 4-alkylbenzothiazolo[2,3-c][1,2,4,6]thiatriazine-1,3,3-trioxides and 4-alkylbenzothiazolo-[3,2-b][1,2,4,6]thiatriazine-1,1,3-trioxides with CSI or PCPCSC in the presence of a tertiary amine base. Monocyclic mesoionic compounds were also synthesized. Mesoionic [1,2,4,6]thiatriazine-1,1,3-trioxides were obtained from the reaction of N,N``-disubstituted amidines with CSI or PCPCSC in the presence of ethyldiisopropylamine in chloroform at room temperature. CSI and PCPCSC were good reagents for the synthesis of mesoionic compounds with 1,3-dinitrogen nucleophiles in the presence of ethyldiisopropylamine under mild conditions.
Advisors
Oh, Dong-YoungKim, Sung-Gak오동영김성각
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1987
Identifier
60973/325007 / 000825006
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 1987.2, [ viii, 100 p. ]

URI
http://hdl.handle.net/10203/31269
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=60973&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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