Utility of (p-sulfonamidophenyl)azomalononitrile, and ethyl acetoacetate in synthesis of fused azole and azines derivatives II

被引:10
作者
Hassanien, AA [1 ]
Amr, AE
Ghozlan, SAS
机构
[1] Suez Canal Univ, Fac Educ, Dept Chem, Al Arish, Egypt
[2] Natl Res Ctr, Dept Appl Organ Chem, Cairo, Egypt
[3] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt
关键词
(p-sulfonamidophenyl)azomalononitrile; ellylacetoacetate; 2-cyanoacetohydrazides; triazolol[1,5-a]pyrimidines and azines;
D O I
10.1002/jccs.200000176
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
[(p-Sulfonamidophenyl)azo]malononitrile (1a,b) reacted with N-cyclohexanemethylidene-2-cyano-acetohydrazide, N'-arylmethylidene-2-cyanoacetohydrazide (3a-c), S-methylthiourea and hydrazine hydrate to afford [1,2,4]triazolo-[1,5-alpha ]pyridinone derivatives (2a,b) & (4a-c), substituted pyrimidines 5a,b and 6a,b. The corresponding pyridazinones 7a,b were synthesized from the reaction of 1c,d with ethyl cyanoacetate. Compound 7a,b reacted with elemental sulfur to yield 8a,b. Compound 6a underwent cycloaddition with alpha -cinnamonitrile 9a-e to yield 11a-c, 14 and 15. Also, compound 6a reacted with beta -ketoester and 1,3-diketones to give 16, 17 and 18.
引用
收藏
页码:1273 / 1278
页数:6
相关论文
共 22 条
[11]  
HASSANIEN AA, 1999, J CHEM RES S, V9, P129
[12]  
HGEN V, 1989, Patent No. 287263
[13]   BASE-INDUCED CYCLOADDITION OF N-(TOSYLMETHYL)IMINO COMPOUNDS TO MICHAEL ACCEPTORS - SYNTHESIS OF 2,3,4-TRISUBSTITUTED PYRROLES [J].
HOUWING, HA ;
VANLEUSEN, AM .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (06) :1127-1132
[14]  
JAIN R, 1991, J INDIAN CHEM SOC, V68, P415
[15]  
JOULE JA, 1995, HETEROCYCLIC CHEM, P426
[16]  
Mandell G. L., 1996, GOODMAN GILMANS PHAR, P1057
[17]   3-SUBSTITUTED 5,7-DIMETHYLPYRAZOLO[1,5-A]PYRIMIDINES, 3',5'-CYCLIC-AMP PHOSPHODIESTERASE INHIBITORS .1. [J].
NOVINSON, T ;
HANSON, R ;
DIMMITT, MK ;
SIMON, LN ;
ROBINS, RK ;
OBRIEN, DE .
JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (06) :645-648
[18]   ADENOSINE CYCLIC 3',5'-MONOPHOSPHATE PHOSPHODIESTERASE INHIBITORS .2. 3-SUBSTITUTED 5,7-DIALKYLPYRAZOLO[1,5-A]PYRIMIDINES [J].
NOVINSON, T ;
MILLER, JP ;
SCHOLTEN, M ;
ROBINS, RK ;
SIMON, LN ;
OBRIEN, DE ;
MEYER, RB .
JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (05) :460-464
[19]   THIENO[2,3-D]PYRIMIDINES AS POTENTIAL CHEMOTHERAPEUTIC-AGENTS [J].
RAM, VJ .
ARCHIV DER PHARMAZIE, 1979, 312 (01) :19-25
[20]   STUDIES ON FUSED AZOLES - SYNTHESIS OF SEVERAL NEW POLYFUNCTIONALLY SUBSTITUTED FUSED PYRAZOLES [J].
SADEK, KU ;
SELIM, MA ;
ELNAGDI, MH ;
OTTO, HH .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (10) :2927-2930