Unprecedented two-step synthesis of symmetrical diarylamines from 2-alkyl-1,3-dinitropropanes

被引:15
作者
Ballini, R
Barboni, L
Femoni, C
Giarlo, G
Palmieri, A
机构
[1] Univ Camerino, Dipartimento Sci Chim, I-63032 Camerino, Italy
[2] Univ Bologna, Dipartimento Chim Fis & Inorgan, I-40136 Bologna, Italy
关键词
diarylamines; aromatization; 1,3-dinitropropanes; one-pot synthesis;
D O I
10.1016/j.tetlet.2006.02.027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This letter reports a new, two-step synthesis of symmetrical diarylamincs from 1,3-dinitroproparics, by their reaction with acrolein under basic conditions (Al2O3, neat), followed by aromatisation of the obtained 2,4-dinitrocyclohexanols, through their treatment with four equivalents of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), in acetonitrile as a solvent. and warming overnight at 60 degrees C. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2295 / 2297
页数:3
相关论文
共 40 条
[1]   THE COPPER CATALYZED REACTION OF SODIUM METHOXIDE WITH ARYL BROMIDES - A MECHANISTIC STUDY LEADING TO A FACILE SYNTHESIS OF ANISOLE DERIVATIVES [J].
AALTEN, HL ;
VANKOTEN, G ;
GROVE, DM ;
KUILMAN, T ;
PIEKSTRA, OG ;
HULSHOF, LA ;
SHELDON, RA .
TETRAHEDRON, 1989, 45 (17) :5565-5578
[2]   One-pot synthesis of 3-alkyl-2,4-dinitrocyclohexanols, under solventless conditions using basic alumina [J].
Ballini, R ;
Barboni, L ;
Fiorini, D ;
Giarlo, G ;
Palmieri, A .
GREEN CHEMISTRY, 2005, 7 (12) :828-829
[3]   One pot synthesis of 3,5-alkylated acetophenone and methyl benzoate derivatives via an anionic domino process [J].
Ballini, R ;
Barboni, L ;
Fiorini, D ;
Giarlo, G ;
Palmieri, A .
CHEMICAL COMMUNICATIONS, 2005, (20) :2633-2634
[4]   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
[5]   Nitroalkanes as a new, convenient source of 1-acyl-2,5-dialkylbenzene derivatives, in two steps [J].
Ballini, R ;
Barboni, L ;
Bosica, G .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6261-6263
[6]   AROMATIC BENZENE COMPOUNDS FROM ACYCLIC PRECURSORS [J].
BAMFIELD, P ;
GORDON, PF .
CHEMICAL SOCIETY REVIEWS, 1984, 13 (04) :441-488
[7]   New triarylamine-containing polymers as hole transport materials in organic light-emitting diodes: Effect of polymer structure and cross-linking on device characteristics [J].
Bellmann, E ;
Shaheen, SE ;
Thayumanavan, S ;
Barlow, S ;
Grubbs, RH ;
Marder, SR ;
Kippelen, B ;
Peyghambarian, N .
CHEMISTRY OF MATERIALS, 1998, 10 (06) :1668-1676
[8]   [5+1] annulation: A synthetic strategy for highly substituted phenols and cyclohexenones [J].
Bi, XH ;
Dong, DW ;
Liu, Q ;
Pan, W ;
Zhao, L ;
Li, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4578-4579
[9]   FORMATION OF 6-MEMBERED AROMATIC RINGS BY CYCLIALKYLATION OF SOME ALDEHYDES AND KETONES [J].
BRADSHER, CK .
CHEMICAL REVIEWS, 1987, 87 (06) :1277-1297
[10]   THE REACTION OF NITROBENZENES WITH SODIUM-BOROHYDRIDE - A NOVEL REDUCTIVE COUPLING TO DIPHENYLAMINE DERIVATIVES [J].
DALE, J ;
VIKERSVEEN, L .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1988, 42 (06) :354-361