A novel combination of (diacetoxyiodo)benzene and tert-butylhydroperoxide for the facile oxidative dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones

被引:26
作者
Karade, Nandkishor N. [1 ]
Gampawar, Sumit V. [1 ]
Kondre, Jeevan M. [1 ]
Tiwari, Girdharilal B. [1 ]
机构
[1] Swami Ramanand Teerth Marathwada Univ, Sch Chem Sci, Nanded 431606, Maharashtra, India
关键词
Biginelli reaction; Dehydrogenation; 1,2-Dihydropyrimidine; Hypervalent iodine; (Diacetoxyiodo)benzene; tert-Butylhydroperoxide;
D O I
10.1016/j.tetlet.2008.09.045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A clean and efficient oxidative dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones to 1,2-dihydropyrimidines has been achieved through a novel combination of (diacetoxyiodo)benzene and tert-butylhydroperoxide in CH2Cl2. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6698 / 6700
页数:3
相关论文
共 40 条
[21]   Organohypervalent iodine: Development, applications, and future directions [J].
Moriarty, RM .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :2893-2903
[22]   Oxidative aromatization of 1,3,5-trisubstituted pyrazolines and hantzsch 1,4-dihydropyridines by Pd/C in acetic acid [J].
Nakamichi, N ;
Kawashita, Y ;
Hayashi, M .
ORGANIC LETTERS, 2002, 4 (22) :3955-3957
[23]   Tetrahydrofuranylation of alcohols catalyzed by alkylperoxy-λ3-iodane and carbon tetrachloride [J].
Ochiai, M ;
Sueda, T .
TETRAHEDRON LETTERS, 2004, 45 (18) :3557-3559
[24]   On the reaction of 3,4-dihydropyrimidones with nitric acid. Preparation and X-ray structure analysis of a stable nitrolic acid [J].
Puchala, A ;
Belaj, F ;
Bergman, J ;
Kappe, CO .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (06) :1345-1352
[25]   Deazapurine solid-phase synthesis:: Construction of 3-substituted pyrrolo[3,2-d]pyrimidine-6-carboxylates on cross-linked polystyrene bearing a cysteamine linker [J].
Rombouts, FJR ;
Fridkin, G ;
Lubell, WD .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (04) :589-598
[26]  
SAUSINS A, 1988, HETEROCYCLES, V27, P291
[27]   Regioselective dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones mediated by ceric ammonium nitrate [J].
Shanmugam, P. ;
Perumal, P. T. .
TETRAHEDRON, 2006, 62 (41) :9726-9734
[28]   Hypervalent iodine oxidation of 1,3,5-tri-substituted pyrazolines: A facile synthesis of 1,3,5-trisubstituted pyrazoles [J].
Singh, SP ;
Kumar, D ;
Prakash, O ;
Kapoor, RP .
SYNTHETIC COMMUNICATIONS, 1997, 27 (15) :2683-2689
[29]  
Slavinskaya V.A., 1978, Patent, Patent No. [632695, 632,695]
[30]   Polymer-supported hypervalent iodine reagents [J].
Togo, H ;
Sakuratani, K .
SYNLETT, 2002, (12) :1966-1975