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

来源：

RSC ADVANCES | 2016年 / 6卷 / 58期

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

页码：52700 / 52709

页数：10

共 39 条

[21]

Mason T.J., 1991, Practical Sonochemistry: User's Guide To Applications

[22]

Mason T.J., 2002, SYNTHESIS, V61

[23]

Mason TJ, 1988, SONOCHEMISTRY THEORY

[24] An Approach to Azabicyclo[n.3.1]alkanes by Double Mannich Reaction [J].

Mityuk, Andrey P. ;

Denisenko, Aleksandr V. ;

Dacenko, Oleksandr P. ;

Grygorenko, Oleksandr O. ;

Mykhailiuk, Pavel K. ;

Volochnyuk, Dmitriy M. ;

Shishkin, Oleg V. ;

Tolmacheva, Andrey A. .

SYNTHESIS-STUTTGART, 2010, (03) :493-497

[25] Unveiling reliable catalysts for the asymmetric nitroaldol (Henry) reaction [J].

Palomo, C ;

Oiarbide, M ;

Mielgo, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (41) :5442-5444

[26] Stereospecific synthesis of oximes and oxime ethers of 3-azabicycles: A SAR study towards antimicrobial agents [J].

Parthiban, Paramasivam ;

Rathika, Paramasivam ;

Ramkumar, Venkatachalam ;

Son, Se Mo ;

Jeong, Yeon Tae .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (05) :1642-1647

[27] Synthesis, stereochemistry and antimicrobial studies of novel oxime ethers of aza/diazabicycles [J].

Parthiban, Paramasivam ;

Aridoss, Gopalakrishnan ;

Rathika, Paramasivam ;

Ramkumar, Venkatachalam ;

Kabilan, Senthamaraikannan .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (24) :6981-6985

[28]

Pelletier S. W., 1970, CHEM ALKALOIDS, P503

[29]

Perumal R.V., 2001, Indian Drugs, V38, P156

[30] Design, synthesis and biological evaluation of novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-1,3-thiazolidin-4-ones as a new class of antimicrobial agents [J].

Ramachandran, R. ;

Rani, M. ;

Kabilan, S. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (10) :2819-2823

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