Microwave-assisted cyclocondensation: a rapid and solvent-free synthesis of 3-benzyl-2H-pyrido[1,2-a]pyrimidin-2-one derivatives

Satyanarayana, S.; Kumar, K. Praveen; Reddy, P. Lakshmi; Narender, R.; Narasimhulu, G.; Reddy, B. V. Subba

doi:10.1016/j.tetlet.2013.06.138

Cited by 12 publications

(5 citation statements)

References 48 publications

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“…Analytical data are in very good agreement with reported data. 27 Yield 0.219g (93%), beige, 1 H NMR (300 MHz, DMSO-d 6 ): δ 8.22 (s, 1H), 8.16 (d, J = 6.7 Hz, 1H), 7.65 (t, J = 7.9 Hz, 1H), 7.30–7.20 (m, 5H), 7.15 (d, J = 6.1 Hz, 1H), 6.93 (t, J = 6.6 Hz, 1H), 3.72 (s, 2H), 13 C NMR (75 MHz, DMSO-d 6 ): δ = 167.6, 151.1, 139.2, 136.9, 136.7, 134.4, 129.3, 128.7, 127.9, 126.6, 122.9, 113.1, 34.1. HRMS (ESI-FTMS Mass (m/z): C 15 H 13 N 2 O [M+H]calc = 237.1022, [M+H]expt = 237.1025.…”

Section: Methodsmentioning

confidence: 99%

“…21 Microwave assisted neat reaction has also been reported to synthesize 2H-pyrido[1,2-a]pyrimidin-2-ones using the same starting materials. 22 Michael addition of 2-aminopyridines on acetylene-derived electrophiles have been used to synthesize these fused pyridopyrimidinones by many groups. 23, 24 Chichetti et al have reported the solvent-free microwave synthesis of novel 6-hydroxypyrimidin-4(1H)-one derivatives using arylmalonates.…”

Section: Introductionmentioning

confidence: 99%

“…25 Su et al have reported the synthesis of these heterocycles by using Vilsmeier reagent. 26 Above methods require, activated Baylis-Hillman adducts, 21, 27 microwave assistance, 22, 25 and added reagents. 23, 24, 26 In our effort to develop domino methodologies to synthesize novel heterocycles, 28, 29 herein, we present hexafluoroisopropanol (HFIP) mediated sustainable design, reagent or catalyst free, and negligible by product formation for the synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones by using 2-aminopyridines and unactivated BH-adducts.…”

Section: Introductionmentioning

confidence: 99%

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Hexafluoroisopropanol mediated benign synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones by using a domino protocol

et al. 2017

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Domino strategy has been used for the synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones. Four sequential reactions: aza-Michael addition, water elimination, intramolecular acyl substitution, and [1,3]-H shift were observed in this domino protocol. Hexafluoroisopropanol is used as a promotor and recyclable solvent in this cascade process. Availability of inexpensive 2-aminopyridines and wide variety of Michael acceptors such as commercially available acrylates and unactivated Baylis-Hillman adducts makes this methodology a huge reservoir of novel fused N-heterocycles as bioactive and potential therapeutic agents. The reaction mechanism has been proposed and rationalized by density functional theory calculation. Products are obtained up to 95% yield.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Hexafluoroisopropanol mediated benign synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones by using a domino protocol

et al. 2017

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“…Organic synthesis using microwave technology has been largely employed, as it can accelerate the reaction time as a consequence of an increase in heating that cannot be achieved with conventional heating [44]. This is what happened in Baozhi's [45] synthesis of p-methylcalix [6] arene.…”

Section: Green Synthesis Proceduresmentioning

confidence: 99%

Green Synthesis of Oligomer Calixarenes

Sardjono¹,

Rachmawati²

2017

Green Chemical Processing and Synthesis

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The synthesis of calixarenes can be conventionally done by heating at high temperature for a few hours and using various solvents in large quantities. The greener synthesis can be done with microwave-assisted synthesis and the solvent-free method, where both of these methods can reduce reaction time, energy use, solvent, and waste, with a higher percentage yield than that from the conventional synthesis method, making the synthesis of cyclic oligomer calixarenes and their derivatives more environmentally friendly.

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“…The literature refers to new methods of production of pyrimidine derivatives and theirv ibhibiting properties in respect of various disease-producing factors [1][2][3][4][5][6][7][8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Research Into One-Step Three Component Reaction of Some Ylidenecyanoacetamides (Or Ylidenemalononitriles), Malononitrile and 1,3-Diaminopropane

Naghiyev¹

2019

Chemical Problems

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The one-step interaction of substituted ylidenecyanoacetamides (or ylidenemalononitriles), malononitrile and 1,3-diaminopropane was carried out in methanol environment at room temperature and it established the formation of new substituted dihydropyridopyrimidine derivatives. It also revealed that under the same conditions through the use of one-step threecomponent reaction of pyridylidenecyanoacetamide (or pyridylidenemalononitrile), 2-chloro-5nitrobenzylidenecyanoacetamide (or 2-chloro-5-nitrobenzylidenemalononitrile), 2,6dichlorobenzylidenecyanoacetamide (or 2,6-dichlorobenzylidenemalononitrile), malononitrile and 1,3-diaminopropane there formed substituted derivatives not of dihydropyridopyrimidine but tetrahydropyridopyrimidine. Structures of all synthesized compounds were verified by NMR and X-Ray spectroscopy.

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Microwave-assisted cyclocondensation: a rapid and solvent-free synthesis of 3-benzyl-2H-pyrido[1,2-a]pyrimidin-2-one derivatives

Cited by 12 publications

References 48 publications

Hexafluoroisopropanol mediated benign synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones by using a domino protocol

Hexafluoroisopropanol mediated benign synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones by using a domino protocol

Green Synthesis of Oligomer Calixarenes

Research Into One-Step Three Component Reaction of Some Ylidenecyanoacetamides (Or Ylidenemalononitriles), Malononitrile and 1,3-Diaminopropane

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