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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 46, Number 4
JKCSEZ 46(4)
August 20, 2002 

A Synthesis of 1,4-Thiazine Carboxanilide: Neighboring Group Participation in Pummerer Reaction

1,4-Thiazine Carboxanilide의 합성 : Pummerer 반응에서의 인접기 참여효과
Hoh-Gyu Hahn, Kee Dal Nam, Heduck Mah

한호경, 남기달, 마희덕
새로운 α,β-불포화Carboxanilide계열의 살균제를 개발을 목적으로 4-acetyl-3-methyl-N-phenyl-1,4-thiazine-2-Carboxamide(6)의 합성에 대하여 기술하였다. Dihydro-1,4-thiazine methyl ester 11을 산화하여 생성된 sulfoxide 7을 Pummerer 반응하여 α-acetoxy dihydro-1,4-thiazine 10a를 얻었다. 반며에 Dihydro-1,4-thiazine Carboxanilide sulfoxide14는 동일한 반응조건 하에서 중간체 sulfonium ion의 carboxanilide기가 관여한 vinylogous Pummerer 반응의 전위에 의하여 중간체를 15를 통하여 acetoxymethyl dihydro-1,4-thiazine 18이 생성되었다. 1,4-Thiazine carboxanilide 6은 α-acetoxy dihydro-1,4-thiazine 10a를 산촉매로 처리한 다음 생성된 21a를 가수분해하고 아닐린과 결합하여 합성하였다

For the purpose of development of new agrochemical fungicide of α,β-unsaturated carboxanilide series a synthesis of 4-acetyl-3-methyl-N-phenyl-1,4-thiazine-2-carboxamide (6) is described. Pummerer reaction of sulfoxide 7 obtained by sulfoxidation of dihydro-1,4-thiazine methyl ester 11 gave α-acetoxy dihydro-1,4-thiazine 10a. Under the same reaction conditions, dihydro-1,4-thiazine carboxanilide sulfoxide 14 was converted to acetoxymethyl dihydro-1,4-thiazine 18 through vinylogous Pummerer reaction involving carboxanilide of sulfonium ion through intermediate 15.1,4-Thiazine carboxanilide 6 was synthesized from the treatment of α-acetoxy dihydro-1,4-thiazine 10a with acid cat-alyst followed by hydrolysis and then the reaction with aniline.

330 - 335
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