Literature DB >> 20356095

Four-component domino reaction providing an easy access to multifunctionalized tricyclo[6.2.2.0(1,6)]dodecane derivatives.

Bo Jiang1, Chao Li, Feng Shi, Shu-Jiang Tu, Parminder Kaur, Walter Wever, Guigen Li.   

Abstract

A novel four-component domino reaction has been discovered. The reaction is easy to perform simply by mixing four common reactants and Cs(2)CO(3) in ethylene glycol under microwave heating. The reaction proceeds at fast rates and can be finished within 15-24 min, which makes workup convenient. Four stereogenic centers with one quaternary carbon-amino function have been controlled completely. The stereochemistry has been unequivocally determined by X-ray structural analysis. The resulting tricyclo[6.2.2.0(1,6)]dodecane derivatives are of importance for organic and medicinal research.

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Year:  2010        PMID: 20356095      PMCID: PMC2862086          DOI: 10.1021/jo1002278

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  24 in total

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Authors:  Scott A Snyder; Steven P Breazzano; Audrey G Ross; Yunqing Lin; Alexandros L Zografos
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6.  Four-component domino reaction leading to multifunctionalized quinazolines.

Authors:  Bo Jiang; Shu-Jiang Tu; Parminder Kaur; Walter Wever; Guigen Li
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

7.  The atom economy--a search for synthetic efficiency.

Authors:  B M Trost
Journal:  Science       Date:  1991-12-06       Impact factor: 47.728

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Authors:  Yong Huang; Abbas M Walji; Catharine H Larsen; David W C MacMillan
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9.  Multicomponent cycloadditions: the four-component [5+1+2+1] cycloaddition of vinylcyclopropanes, alkynes, and CO.

Authors:  Paul A Wender; Gabriel G Gamber; Robert D Hubbard; Son M Pham; Lei Zhang
Journal:  J Am Chem Soc       Date:  2005-03-09       Impact factor: 15.419

10.  Highly diastereoselective domino synthesis of 6-spirosubstituted pyrido[2,3-d]pyrimidine derivatives in water.

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  8 in total

1.  Microwave-assisted multicomponent reaction in water leading to highly regioselective formation of benzo[f]azulen-1-ones.

Authors:  Shu-Liang Wang; Chuang Cheng; Fei-Yue Wu; Bo Jiang; Feng Shi; Shu-Jiang Tu; Trideep Rajale; Guigen Li
Journal:  Tetrahedron       Date:  2011-06-24       Impact factor: 2.457

2.  Efficient domino approaches to multifunctionalized fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones.

Authors:  Bo Jiang; Qiu-Yun Li; Hao Zhang; Shu-Jiang Tu; Suresh Pindi; Guigen Li
Journal:  Org Lett       Date:  2012-01-19       Impact factor: 6.005

3.  A multi-component domino reaction for the direct access to polyfunctionalized indoles via intermolecular allylic esterification and indolation.

Authors:  Bo Jiang; Mian-Shuai Yi; Feng Shi; Shu-Jiang Tu; Suresh Pindi; Patrick McDowell; Guigen Li
Journal:  Chem Commun (Camb)       Date:  2011-10-31       Impact factor: 6.222

4.  Domino constructions of pentacyclic indeno[2,1-c]quinolines and pyrano[4,3-b]oxepines by [4+1]/[3+2+1]/[5+1] and [4+3] multiple cyclizations.

Authors:  Bo Jiang; Bao-Ming Feng; Shu-Liang Wang; Shu-Jiang Tu; Guigen Li
Journal:  Chemistry       Date:  2012-07-05       Impact factor: 5.236

5.  A one-pot multicomponent strategy for stereospecific construction of tricyclic pyrrolo[1,2-a]quinolines.

Authors:  Tuan-Jie Li; Hong-Mei Yin; Chang-Sheng Yao; Xiang-Shan Wang; Bo Jiang; Shu-Jiang Tu; Guigen Li
Journal:  Chem Commun (Camb)       Date:  2012-12-21       Impact factor: 6.222

6.  Highly selective domino multicyclizations for forming polycyclic fused acridines and azaheterocyclic skeletons.

Authors:  Bo Jiang; Xue Wang; Hai-Wei Xu; Man-Su Tu; Shu-Jiang Tu; Guigen Li
Journal:  Org Lett       Date:  2013-03-18       Impact factor: 6.005

7.  Metal-free [3 + 2 + 1]/[2 + 2 + 1] biscyclization: stereospecific construction with concomitant functionalization of indolizin-5(1H)-one.

Authors:  Tuan-Jie Li; Zhong-Qiu Liu; Hong-Mei Yin; Chang-Sheng Yao; Bo Jiang; Xiang-Shan Wang; Shu-Jiang Tu; Xiu-Ling Li; Guigen Li
Journal:  J Org Chem       Date:  2013-11-07       Impact factor: 4.354

8.  Allylic amination and N-arylation-based domino reactions providing rapid three-component strategies to fused pyrroles with different substituted patterns.

Authors:  Bo Jiang; Ying Li; Man-Su Tu; Shu-Liang Wang; Shu-Jiang Tu; Guigen Li
Journal:  J Org Chem       Date:  2012-08-13       Impact factor: 4.354

  8 in total

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