Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes catalyzed by tetramethylguanidine

Kalla, Reddi Mohan Naidu; Byeon, Seong Jin; Heo, Min; Kim, Il

doi:10.1016/j.tet.2013.10.052

Cited by 53 publications

(21 citation statements)

References 35 publications

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“…In this respect, although numerous organocatalyzed racemic syntheses of this family of compounds can be found in the literature [22][23][24][25][26][27][28][29][30][31][32][33], only scarce examples following an enantioselective approach have been reported to date [34].…”

Section: Figurementioning

confidence: 99%

Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives

2015

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Abstract:The structural motif that results from the fusion of a benzene ring to a heterocyclic pyran ring, known as chromene, is broadly found in nature and it has been reported to be associated with a wide range of biological activity. Moreover, asymmetric organocatalysis is a discipline in expansion that is already recognized as a well-established tool for obtaining enantiomerically enriched compounds. This review covers the particular case of the asymmetric synthesis of 2-amino-3-cyano-4H-chromenes using organocatalysis. Herein, we show the most illustrative examples of the methods developed by diverse research groups, following a classification based on these five different approaches: (1) addition of naphthol compounds to substituted α,α-dicyanoolefins; (2) addition of malononitrile to substituted o-vinylphenols; (3) addition of malononitrile to N-protected o-iminophenols; (4) Michael addition of nucleophiles to 2-iminochromene derivatives; and (5) organocatalyzed formal [4+2] cycloaddition reaction. In most cases, chiral thioureas have been found to be effective catalysts to promote the synthetic processes, and generally a bifunctional mode of action has been envisioned for them. In addition, squaramides and cinchona derivatives have been occasionally used as suitable catalysts for the substrates activation.

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Section: Figurementioning

confidence: 99%

Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives

2015

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“…The MCRs has been attracting attention of numerous chemists because it is a powerful technique for synthesis of derivatives with biological activity and pharmaceutical properties [1]. To develop clean, easy and eco-friendly method for the synthesis of organic moiety with significant biological activity is the further most important objective in synthetic organic chemistry and is also helpful in research area of green or sustainable chemistry [2].…”

Section: Introductionmentioning

confidence: 99%

Microwave Assisted One Pot Synthesis of 3,4-Dihydropyrano[c]chromene Derivatives using [Emim]OH Ionic Liquid as Novel Catalyst

et al. 2019

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One-pot efficient protocol to the synthesis of 2-amino-5-oxo-4,5-dihydropyrano(3,2-c)chromene-3-carbonitrile derivatives via condensation of various aryl aldehydes, dicyanomethane and 4-hydroxycoumarin in presence of Emim hydroxide as an excellent homogeneous liquid catalyst. The key advantages of this methodology are mild reaction conditions, novel catalyst, short reaction time, eco-friendly, easy work-up procedure and high yield of isolation of derivatives.

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“…For variety oriented synthesis, the structure of these bioactive molecules could provide chances for drug design in three important regions (the aromatic ring of the benzopyran, substitution at C2-amine, and the substituted group at C4 position). Therefore, substantial efforts have been made over the past decades for the synthesis of 2 amino-4H-chromenes (Dong et al, 2011, Gao et al, 2008Neelakandan et al, 2011;Ding et al, 2010;Gao et al, 2013), which is accomplished using various catalysts including diethylamine (Kulakarni et al, 2012), ethylenediamine diacetate (Kolla et al, 2012), I 2 (Rajaskhar et al, 2012), PEG (Das et al, 2011), β-cyclodextrin (Murthy et al, 2010), InCl 3 (Jayashree et al, 2009, Shanthi et al, 2008, Yin et al, 2013, guanidine (Kalla et al, 2013), ammonium acetate (Fujimoto et al, 1977), Al 2 O 3 (Roudier and Foucaud 1984), Zr (KPO 4 ) 2 (Massimo et al, 2005), molecular sieves (Yu et al, 2000), aminosilane-modified Fe 3 O 4 nanoparticles (Safari et al, 2014) and silica-bonded 2-hydroxyethylammonium acetate (HEAA) (Sobhani et al, 2013). However, some of these protocols require complex and expensive catalytic systems, prolonged reaction times and complicated operations.…”

Section: Introductionmentioning

confidence: 99%

One pot synthesis of 2- amino-5-oxo-4-aryl-5, 6, 7, 8-tetrahydro- 4Hchromenes- 3-carboxilic acid ethyl esters

Mahmud

Halim

Ali

et al. 2018

Bangladesh J. Sci. Ind. Res.

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Ethyl esters of 2-cyano-3-arylacrylic acid 1a-b ( a = 3- Br- C6H4, b= 4- OH- C6H4 ) reacted with 5, 5-dimethyl-1, 3-cyclohexane (2b, R = CH3) and 1c-d (c= 3- OH- C6H4, d= 3- NO2- C6H4 ) reacted with 1, 3-cyclohexanedione (2a, R = H) and 5, 5-dimethyl-1, 3-cyclohexanedione (2b, R=CH3) in the presence of alcoholic sodium ethoxide to give the corresponding ethyl esters of 2- amino- 7, 7- dimethyl-5-oxo-4-aryl-5, 6, 7, 8-tetrahydro- 4H- chromenes-3-carboxylic acid 3a-c, 3f and 2- amino-5-oxo-4-aryl-5, 6, 7, 8-tetrahydro- 4H- chromenes-3-carboxilic acid ethyl esters 3d-e. The structures of the compounds 3a-f were confirmed by their ultraviolet (UV), infrared (IR), 1H NMR, 13C NMR, mass spectra and elemental analyses.Bangladesh J. Sci. Ind. Res.53(1), 35-40, 2018

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Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes catalyzed by tetramethylguanidine

Cited by 53 publications

References 35 publications

Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives

Enantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives

Microwave Assisted One Pot Synthesis of 3,4-Dihydropyrano[c]chromene Derivatives using [Emim]OH Ionic Liquid as Novel Catalyst

One pot synthesis of 2- amino-5-oxo-4-aryl-5, 6, 7, 8-tetrahydro- 4Hchromenes- 3-carboxilic acid ethyl esters

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