5-Amino-2H-1,2,4-thiadiazoline-3-one has been prepared from 2-thiobiuret through a oxidative cyclization under basic hydrogen peroxide condition. Lactam-lactim tautomerism of 5-amino-2H-1,2,4-thiadiazoline-3-one has been examined by spectroscopic methods and ab initio molecular orbital calculation. These results were shown that 5-amino-2H-1,2,4-thiadiazoline-3-one exists as lactam form. Reaction conditions for alkylating 5-amino-2H-1,2,4-thiadiazoline-3-one with alkyl halides in the presence of various bases were studied in DMF and $H_2O$-THF two phase system. $Li_2CO_3$ base in DMF method gave best result in this investigation. The alkylation has been taken place at N-2 position. The identification of the product is confirmed by spectral data of IR, $^1H$ NMR and $^13C$ NMR and the comparison of authentic sample, 5-amino-2-methyl-1,2,4-thiadiazolidine-3-one, obtained from the oxidative cyclization of 5-methyl-2-thiobiuret.
Citing 'Tautomerism and Alkylation of 5-Amino-2H-1,2,4-thiadiazoline-3-one
'
@article{ JCGMDC_1995_v39n7_564}
,title={Tautomerism and Alkylation of 5-Amino-2H-1,2,4-thiadiazoline-3-one}
,volume={7}
, number= {7}
, journal={Journal of the Korean Chemical Society}
, publisher={Korean Chemical Society}
, author={Nam Sook, Cho
and
Young Cheol, Park
and
Do Young, Ra
and
Sungkwon, Kang}
, year={1995}
, month={Jul}
TY - JOUR
T2 - Journal of the Korean Chemical Society
AU - Nam Sook, Cho
AU - Young Cheol, Park
AU - Do Young, Ra
AU - Sungkwon, Kang
SN - 1017-2548
TI - Tautomerism and Alkylation of 5-Amino-2H-1,2,4-thiadiazoline-3-one
VL - 39
PB - Korean Chemical Society
PY - 1995
ER -
Nam Sook, C.
,
Young Cheol, P.
,
Do Young, R.
,
&
Sungkwon, K.
( 1995).
Tautomerism and Alkylation of 5-Amino-2H-1,2,4-thiadiazoline-3-one.
Journal of the Korean Chemical Society,
39
(7)
Korean Chemical Society.
Nam Sook, C
,
Young Cheol, P
,
Do Young, R
,
&
Sungkwon, K
1995,
Tautomerism and Alkylation of 5-Amino-2H-1,2,4-thiadiazoline-3-one,
Journal of the Korean Chemical Society,
vol. 7,
no. 7,
[1]
C Nam Sook
,
P Young Cheol
,
R Do Young
,
and
K Sungkwon
,
“Tautomerism and Alkylation of 5-Amino-2H-1,2,4-thiadiazoline-3-one”,
Journal of the Korean Chemical Society,
vol. 7,
no. 7,
Jul
1995.
Nam Sook, Cho
Young Cheol, Park
Do Young, Ra
et al.
“Tautomerism and Alkylation of 5-Amino-2H-1,2,4-thiadiazoline-3-one”
Journal of the Korean Chemical Society,
7.
7
1995:
Nam Sook, C
,
Young Cheol, P
,
Do Young, R
,
Sungkwon, K
Tautomerism and Alkylation of 5-Amino-2H-1,2,4-thiadiazoline-3-one.
Journal of the Korean Chemical Society
[Internet].
1995.
Jul ;
7
(7)
Nam Sook, Cho
,
Young Cheol, Park
,
Do Young, Ra
,
and
Sungkwon, Kang
,
“Tautomerism and Alkylation of 5-Amino-2H-1,2,4-thiadiazoline-3-one.”
Journal of the Korean Chemical Society
7
no.7
()
Jul,
1995):
