An efficient ultrasonic-mediated one-pot synthesis of 2,3,6,7,9-pentaazabicyclo[3.3.1]nonanes via a N,N-dimethylformamide dimethylacetal catalyzed Mannich-like reaction

被引:8
作者
Behbehani, Haider [1 ]
Ibrahim, Hamada Mohamed [1 ]
机构
[1] Kuwait Univ, Fac Sci, Dept Chem, POB 5969, Safat 13060, Kuwait
关键词
4+1 CYCLOADDITION; DERIVATIVES; CHEMISTRY;
D O I
10.1039/c6ra09210a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel and straightforward method for one-pot synthesis of functionalized 2,3,6,7,9-pentaazabicyclo[3.3.1]nonane derivatives has been developed. The process, which involves ultrasonic irradiation promoted Mannich reaction between 3-oxo-2-arylhydrazonopropanals and ammonia in acetic acid, is catalyzed by N,N-dimethylformamide dimethylacetal (DMF-DMA) and generates the target products in 80-93% yields.
引用
收藏
页码:52700 / 52709
页数:10
相关论文
共 39 条
[1]  
[Anonymous], PLANT ALKALOIDS
[2]   Ultrasound-assisted one-pot, three-component synthesis of spiro[indoline-3,4′-pyrazolo[3,4-b]pyridine]-2,6′(1′H)-diones in water [J].
Bazgir, Ayoob ;
Ahadi, Somayeh ;
Ghahremanzadeh, Ramin ;
Khavasi, Hamid Reza ;
Mirzaei, Peiman .
ULTRASONICS SONOCHEMISTRY, 2010, 17 (02) :447-452
[3]   Microwave-assisted synthesis in water: first one-pot synthesis of a novel class of polysubstituted benzo[4,5]imidazo[1,2-b]pyridazines via intramolecular SNAr [J].
Behbehani, Haider ;
Ibrahim, Hamada Mohamed .
RSC ADVANCES, 2015, 5 (108) :89226-89237
[4]   Ultrasound-assisted regio- and stereoselective synthesis of bis-[1′,4′-diaryl-1-oxo-spiro-benzosuberane-2,5′-pyrazoline] derivatives via 1,3-dipolar cycloaddition [J].
Behbehani, Haider ;
Ibrahim, Hamada Mohamed ;
Dawood, Kamal M. .
RSC ADVANCES, 2015, 5 (33) :25642-25649
[5]   A strategy for the synthesis of 2-aryl-3-dimethylaminopyrazolo-[3,4-c]pyridines that utilizes [4+1] cycloaddition reactions of 5-arylazo-2,3,6-trisubstituted pyridines [J].
Behbehani, Haider ;
Ibrahim, Hamada Mohamed .
TETRAHEDRON, 2013, 69 (49) :10535-10543
[6]   Non-concerted nucleophilic [4+1] cycloaddition of (dimethylamino) methoxycarbene to arylazonicotinates in the synthesis of pyrazolo[3,4-c]pyridines and pyrazolo[4′,3′:4,5]pyrido[2,3-d]pyrimidines [J].
Behbehani, Haider ;
Ibrahim, Hamada Mohamed ;
Elnagdi, Mohamed H. .
TETRAHEDRON, 2013, 69 (30) :6176-6184
[7]   Distortional isomerism with copper(I) complexes of 3,7-diazabicyclo[3.3.1]nonane derivatives [J].
Born, Karin ;
Comba, Peter ;
Kerscher, Marion ;
Linti, Gerald ;
Pritzkow, Hans ;
Rohwer, Heidi .
DALTON TRANSACTIONS, 2009, (02) :362-367
[8]   Efficient synthesis of the azabicyclo[3.3.1]nonane ring system in the alkaloid methyllyeaconitine using bis(alkoxymethyl)alkylamines as aminoalkylating agents in a double Mannich reaction [J].
Brimble, MA ;
Brocke, C .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (11) :2385-2396
[9]   Synthesis and transformations of 1,3,5,7-Tetraazabicyclo[3.3.1]nonanes [J].
Bryukhanov, AY ;
Golod, EL .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2002, 72 (08) :1299-1305
[10]   Power ultrasound in organic systhesis: moving cavitational chemistry from academia to innovative and large-scale applications [J].
Cravotto, G ;
Cintas, P .
CHEMICAL SOCIETY REVIEWS, 2006, 35 (02) :180-196