Hexamethylenetetramine as a Cheap and Convenient Alternative Catalyst in the Baylis—Hillman Reaction: Synthesis of Aromatic Compounds with anti‐Malarial Activity.

Souza, Rodrigo O. M. A. de; Meireles, Bruno A.; Aguiar, Lúcia C. S.; Vasconcellos, Mário L. A. A.

doi:10.1002/chin.200445093

Cited by 3 publications

(6 citation statements)

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“…Values reported for coupling constants are first‐order. The Baylis–Hillman adducts 1 – 4 6, 19, 20 and 6 – 10 12, 19, 21, 22 have been synthesised previously. The new compound 3‐hydroxy‐2‐methylene‐3‐(4‐fluorophenyl)propanenitrile (Fig.…”

Section: Methodsmentioning

confidence: 99%

“…In addition, in connection with our efforts towards efficient and cheaper methodologies to synthesise Baylis–Hillman adducts,12, 13 we recently prepared 3‐hydroxy‐2‐methylene‐3‐(4‐nitrophenyl)propanenitrile (Fig. 1; 1 ) in high yields using hexamethylenetetramine (HMT) as a very cheap catalyst 6. Compound 1 had the highest antimalarial activity in a series of aromatic compounds described by Kundu et al 14…”

Section: Introductionmentioning

confidence: 99%

“…In our continuing search for bioactive substances6–10 we have recently described some effective molluscicidal compounds prepared from lapachol 11. In addition, in connection with our efforts towards efficient and cheaper methodologies to synthesise Baylis–Hillman adducts,12, 13 we recently prepared 3‐hydroxy‐2‐methylene‐3‐(4‐nitrophenyl)propanenitrile (Fig.…”

Section: Introductionmentioning

confidence: 99%

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Baylis–Hillman adducts with molluscicidal activity against Biomphalaria glabrata

Vasconcellos

Silva

Câmara

et al. 2006

Pest Management Science

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The molluscicidal activities of ten Baylis-Hillman adducts against Biomphalaria glabrata (Say) snails, the intermediate host of schistosomiasis, have been determined. Nine of these compounds showed significant molluscicidal activity against B. glabrata, falling below the threshold of 100 microg ml(-1) set for potential molluscicidal activity by the World Health Organisation. Among these compounds, 3-hydroxy-2-methylene-3-(4-nitrophenyl)propanenitrile had the highest activity, with LC(50) = 6.64 microg ml(-1).

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Baylis–Hillman adducts with molluscicidal activity against Biomphalaria glabrata

Vasconcellos

Silva

Câmara

et al. 2006

Pest Management Science

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show abstract

“…which can be involved in this reaction (Scheme 3). At the same time, besides aldehydes, ketones and N-p-tosylimines can be used as an electronic receptor reacted with activated olefin [2][3][4][5][6][7][8][9][10][11][12].…”

Section: Dabco Catalyzed Baylis-hillman Reaction In Formation Of Carbmentioning

confidence: 99%

Organic reactions catalyzed by 1, 4-diazabicyclo [2.2.2] octane (DABCO)

Yang

Tian

2008

Front. Chem. China

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The organic reactions catalyzed by 1, 4-diazabicyclo [2.2.2] octane (DABCO) are reviewed. Most of the reactions start conveniently from available substrate and proceed under mild conditions. The reactions are environmentally friendly and the catalyst can be recycled in some cases. The perspectives on DABCO-catalyzed reactions are pointed out. Keywords 1, 4-diazabicyclo [2.2.2] octane (DABCO), organic synthesis, catalysis 1,4-Diazabicyclo [2.2.2] octane (DABCO, Scheme 1), a cage-like compound, is a small diazabicyclic molecule, which has weak alkalescence, medium-hindrance and widely used in organic synthesis reactions. On the one hand, it can serve as a weak base and ligand, for example, reactions of the Nmethylation of indoles and Pd(OAc) 2 /DABCO-catalyzed Stille cross-coupling reaction, etc. On the other hand, it is also a very widely used catalyst in organic synthesis reactions, for example, the Baylis-Hillman reaction, synthesis of three-membered carbocyclic compounds and heterocyclic reactions containing oxygen, nitrogen. According to the types of products, this paper introduces the application of DABCO in organic synthesis in the recent years.

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“…1) [16][17][18][19][20][21][22][23][24][25][26], several protocols have been proposed to accelerate this reaction, such as the use of ultrasound [27], addition of salts [28], high pressure [29], ionic liquids [30][31][32] and microwave irradiation. MBHR are usually slow and the reaction may take from days to weeks for completion depending on the reactivity of the activated alkene, electrophile and catalyst.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Morita-Baylis-Hillman Reaction Under Microwave Irradiation

Souza¹,

Miranda

2010

MROC

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The Morita-Morita-Baylis-Hillman reaction (MMBHR) is one of the most important carbon-carbon bond forming reactions, and involves the selective atom-economical construction of a carbon-carbon bond at the -position of an activated alkene, providing densely functionalized molecules. One of the major drawbacks of the MBHR is the low reaction rate, requiring long reaction times. In this review, the MBHR, in combination with microwave irradiation is summarized for the synthesis of highly functionalized molecules with the advantages of green process and shorter reaction times.

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Hexamethylenetetramine as a Cheap and Convenient Alternative Catalyst in the Baylis—Hillman Reaction: Synthesis of Aromatic Compounds with anti‐Malarial Activity.

Cited by 3 publications

References 0 publications

Baylis–Hillman adducts with molluscicidal activity against Biomphalaria glabrata

Baylis–Hillman adducts with molluscicidal activity against Biomphalaria glabrata

Organic reactions catalyzed by 1, 4-diazabicyclo [2.2.2] octane (DABCO)

Recent Advances in the Morita-Baylis-Hillman Reaction Under Microwave Irradiation

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