Thermolysis of N,N"-1,ω-alkanediyl-bis[N′-organylthiourea] derivatives

被引:12
作者
Hassan, Alaa A. [1 ]
Doepp, Dietrich
机构
[1] Menia Univ, Fac Sci, Dept Chem, El Minia, Egypt
[2] Univ Duisburg Essen, D-47048 Duisburg, Germany
关键词
D O I
10.1002/jhet.5570430311
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
The course of microwave assisted or conventional thermal intramolecular heterocyclization of the title compounds has been found to be dependent on the length of the alkanediyl chain. While 1,3-propanediyl-bisthioureas 5a-c gave both 2-thioxoperhydropyrimidine-1-carbothioamides 8a-c and 8-amino-3,4,5,6-tetrahydro-1,3,7-thiadiazocine-2-thiones 10a-c, thermolysis of 1,4-butanediyl-bisthioureas 6a-c and 1,6-hexanediyl-bisthioureas 7a-c under the same conditions gave solely 9-amino-4,5,6,7-tetrahydro-1,3,8-thiadiazonine-2-thiones 11a-c and 11-amino-1-thia-3,10-diazacycloundec-10-ene-2-thiones 12a-c, respectively. Symmetric N,N'-diorganylthioureas 4a-c were formed in all cases as minor byproducts.
引用
收藏
页码:593 / 598
页数:6
相关论文
共 25 条
[1]
Synthesis of symmetrical N,N′-disubstituted thioureas and heterocyclic thiones from amines and CS2 over a ZnO/Al2O3 composite as heterogeneous and reusable catalyst [J].
Ballabeni, M ;
Ballini, R ;
Bigi, F ;
Maggi, R ;
Parrini, M ;
Predieri, G ;
Sartori, G .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1029-1032
[2]
CLEAVAGE OF SUBSTITUTED THIOUREAS [J].
BINDER, H .
MONATSHEFTE FUR CHEMIE, 1967, 98 (02) :431-&
[3]
Blanco JLJ, 1999, SYNTHESIS-STUTTGART, P1907
[4]
Duus F., 1979, COMPREHENSIVE ORGANI, V3, P452
[5]
ELIEL EL, 1994, STEREOCHEMISTRY ORGA, P770
[6]
THERMOLYSIS OF SOME THIOUREA DERIVATIVES [J].
GABER, AEM ;
ALY, MM ;
ATALLA, AA .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1991, 56 (10) :2183-2187
[7]
Thermal fragmentation of some aryl thiourea derivatives [J].
Gaber, AEM ;
Mohamed, OS .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2001, 174 :193-199
[8]
GOLDING BT, 1981, J CHEM RES S, V11, P342
[9]
GUENDEL W, 1964, Patent No. 1183069
[10]
Solid-phase synthesis of arginine-containing peptides and fluorogenic substrates using a side-chain anchoring approach [J].
Hamzé, A ;
Martinez, J ;
Hernandez, JF .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24) :8394-8402