One-pot synthesis of 3-alkyl-2,4-dinitrocyclohexanols, under solventless conditions using basic alumina

被引:22
作者
Ballini, R [1 ]
Barboni, L [1 ]
Fiorini, D [1 ]
Giarlo, G [1 ]
Palmieri, A [1 ]
机构
[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy
关键词
D O I
10.1039/b512617g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
3-Alkyl-2,4-dinitrocyclohexanols can be prepared in a one-pot procedure by reaction of 1,3-dinitroalkanes with acrolein, catalysed by basic alumina and in the absence of any solvent. The synthesis proceeds using tandem Michael/nitroaldol (Henry) reactions and allows satisfactory to good yields of the title compounds. Moreover, several functionalities can be preserved under our conditions.
引用
收藏
页码:828 / 829
页数:2
相关论文
共 22 条
[1]   Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results [J].
Ballini, R ;
Bosica, G ;
Fiorini, D ;
Palmieri, A ;
Petrini, M .
CHEMICAL REVIEWS, 2005, 105 (03) :933-971
[2]   One-pot synthesis of 1,3-dinitroalkanes under heterogeneous catalysis [J].
Ballini, R ;
Bosica, G ;
Fiorini, D ;
Palmieri, A .
SYNTHESIS-STUTTGART, 2004, (12) :1938-1940
[3]   Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction) [J].
Ballini, R ;
Petrini, M .
TETRAHEDRON, 2004, 60 (05) :1017-1047
[4]   Use of heterogeneous catalyst KG-60-NEt2 in Michael and Henry reactions involving nitroalkanes [J].
Ballini, R ;
Bosica, G ;
Livi, D ;
Palmieri, A ;
Maggi, R ;
Sartori, G .
TETRAHEDRON LETTERS, 2003, 44 (11) :2271-2273
[5]   MCM-41-TBD as a new, efficient, supported heterogeneous catalyst for the synthesis of thioureas [J].
Ballini, R ;
Bosica, G ;
Fiorini, D ;
Maggi, R ;
Righi, P ;
Sartori, G ;
Sartorio, R .
TETRAHEDRON LETTERS, 2002, 43 (47) :8445-8447
[6]   Clay-catalysed solventless synthesis of trans-chalcones [J].
Ballini, R ;
Bosica, G ;
Maggi, R ;
Ricciutelli, M ;
Righi, P ;
Sartori, G ;
Sartorio, R .
GREEN CHEMISTRY, 2001, 3 (04) :178-180
[7]   Zeolite as base catalyst: Nitroaldolic condensation [J].
Ballini, R ;
Bigi, F ;
Gogni, E ;
Maggi, R ;
Sartori, G .
JOURNAL OF CATALYSIS, 2000, 191 (02) :348-353
[8]  
Clark J.H., 1995, CHEM WASTE MINIMISAT
[9]   Environmentally friendly catalytic methods [J].
Clark, JH ;
Macquarrie, DJ .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (05) :303-&
[10]  
Corey E.J., 1989, The Logic of Chemical Synthesis