Abstract
For the first time, derivatives of 1,2,4-thiadiazoles have been obtained by the reaction of [bis(acyloxy)iodo]arenes with 1-monosubstituted thioureas. 1-Acetylthiourea is subject to intermolecular azacyclization to form 3,5-bis-(acetylamino)-1,2,4-thiadiazole in reaction with [bis(acyloxy)iodo]benzene. 1-Phenylthiourea forms 3,5-bis-(phenylamino)-1,2,4-thiadiazole in a single-stage reaction with (diacetoxyiodo)benzene. The reaction of 1-phenylthiourea with [bis(trifluoroacetoxy)iodo]benzene leads to the formation of 5-imino-4-phenyl-3-phenylamino-4H-1,2,4-thiadiazoline.
| Original language | English |
|---|---|
| Pages (from-to) | 7521-7525 |
| Number of pages | 5 |
| Journal | Tetrahedron |
| Volume | 59 |
| Issue number | 38 |
| DOIs | |
| Publication status | Published - 15 Sep 2003 |
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Keywords
- 1,2,4-thiadiazoles
- Oxidation
- Polyvalent iodine
- Thioureas
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Oxidative azacyclization of 1-monosubstituted thioureas in reaction with [bis(acyloxy)iodo]arenes to form 1,2,4-thiadiazole derivatives. / Mamaeva, Elena A.; Bakibaev, Abdigali A.
In: Tetrahedron, Vol. 59, No. 38, 15.09.2003, p. 7521-7525.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Oxidative azacyclization of 1-monosubstituted thioureas in reaction with [bis(acyloxy)iodo]arenes to form 1,2,4-thiadiazole derivatives
AU - Mamaeva, Elena A.
AU - Bakibaev, Abdigali A.
PY - 2003/9/15
Y1 - 2003/9/15
N2 - For the first time, derivatives of 1,2,4-thiadiazoles have been obtained by the reaction of [bis(acyloxy)iodo]arenes with 1-monosubstituted thioureas. 1-Acetylthiourea is subject to intermolecular azacyclization to form 3,5-bis-(acetylamino)-1,2,4-thiadiazole in reaction with [bis(acyloxy)iodo]benzene. 1-Phenylthiourea forms 3,5-bis-(phenylamino)-1,2,4-thiadiazole in a single-stage reaction with (diacetoxyiodo)benzene. The reaction of 1-phenylthiourea with [bis(trifluoroacetoxy)iodo]benzene leads to the formation of 5-imino-4-phenyl-3-phenylamino-4H-1,2,4-thiadiazoline.
AB - For the first time, derivatives of 1,2,4-thiadiazoles have been obtained by the reaction of [bis(acyloxy)iodo]arenes with 1-monosubstituted thioureas. 1-Acetylthiourea is subject to intermolecular azacyclization to form 3,5-bis-(acetylamino)-1,2,4-thiadiazole in reaction with [bis(acyloxy)iodo]benzene. 1-Phenylthiourea forms 3,5-bis-(phenylamino)-1,2,4-thiadiazole in a single-stage reaction with (diacetoxyiodo)benzene. The reaction of 1-phenylthiourea with [bis(trifluoroacetoxy)iodo]benzene leads to the formation of 5-imino-4-phenyl-3-phenylamino-4H-1,2,4-thiadiazoline.
KW - 1,2,4-thiadiazoles
KW - Oxidation
KW - Polyvalent iodine
KW - Thioureas
UR - http://www.scopus.com/inward/record.url?scp=0041328953&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0041328953&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(03)01176-1
DO - 10.1016/S0040-4020(03)01176-1
M3 - Article
VL - 59
SP - 7521
EP - 7525
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 38
ER -