The Baylis-Hillman Bromides as Versatile Synthons: A Facile One-Pot Synthesis of Indolizine and Benzofused Indolizine Frameworks

Basavaiah, Deevi; Devendar, Badugu; Lenin, Dandamudi V.; Satyanarayana, T.

doi:10.1055/s-0028-1087533

Cited by 77 publications

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“…8 The described reaction is a convenient way to access 1-aryl-2-cyanoindolizines and their πexpanded derivatives under mild conditions despite moderate yields. 8 The described reaction is a convenient way to access 1-aryl-2-cyanoindolizines and their πexpanded derivatives under mild conditions despite moderate yields.…”

Section: From Pyridines With a Free C2 Positionmentioning

confidence: 98%

Recent advances in the synthesis of indolizines and their π-expanded analogues

2016

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Indolizine (pyrrolo[1,2-a]pyridine) is one of the five isomers of indole and it serves as a precursor for widespread indolizidine alkaloids. The straightforward synthesis of indolizines based on classical methodologies such as Scholtz or Chichibabin reactions has overshadowed numerous new strategies that have been revealed especially within the last ten years. The desire to achieve substitution patterns which were hard to build sparked the discovery of completely new pathways, e.g. transition metal-catalyzed reactions and approaches based on oxidative coupling. In this review, selected strategies toward indolizines published since 2005 are briefly summarized, commented upon, compared, and illustrated. The literature discussed here involves reactions based on either pyridine or pyrrole scaffolds, as well as selected methodologies leading to π-expanded indolizines.

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Section: From Pyridines With a Free C2 Positionmentioning

confidence: 98%

Recent advances in the synthesis of indolizines and their π-expanded analogues

2016

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“…[9][10][11][12][13][14][15] We have also demonstrated very high applicability and potential of the Baylis-Hillman adducts in a number of organic transformations leading to the synthesis of different carbocyclic and heterocyclic compounds, including bioactive molecules. [16][17][18][19][20][21] This talk will present our vision, objectives, and endeavors towards the development of this reaction as a source of opportunities, challenges and creativity in synthetic chemistry keeping its applications as the primary goal. …”

Section: -8mentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8] We have been systematically working on various aspects of this reaction for the last 29 years with the main objective of understanding and developing the Baylis-Hillman reaction as a useful and powerful tool in synthetic chemistry. [9][10][11][12][13][14][15][16][17][18][19][20][21] We have in fact, contributed significantly to its growth with respect to all the three essential components. …”

Section: -8mentioning

confidence: 99%

The Baylis-Hillman reaction: Our vision and experience

Basavaiah¹

2013

Proceedings of the 15th Brazilian Meeting on Organic Synthesis Proceedings

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SpeechTo meet the demands of emerging trends, the present day organic chemistry emphasizes the need for discovering new reactions or strategies for construction of carbon-carbon bonds mainly involving the concepts of atom-economy, organocatalysis, and easy generation of useful molecules containing proximal functional groups for assembling the required carbon frameworks. The Baylis-Hillman (also known as the Morita-Baylis-Hillman) reaction is one such organocatalytic atom-economy reaction developed in recent years, for the construction of carbon-carbon bonds leading to the production of diverse classes of molecules having several functional groups in close proximity. It is a three component atom-economy carbon-carbon bond forming reaction between the α-position of activated alkenes and electrophiles under the influence of a catalyst (most commonly an organic catalyst). 1-8These multi-functional molecules, which are usually known as Baylis-Hillman (BH) adducts, showed enormous utility in many directions of synthetic and mechanistic chemistry, clearly demonstrating the power of proximity of the functional groups in molecules. [1][2][3][4][5][6][7][8] We have been systematically working on various aspects of this reaction for the last 29 years with the main objective of understanding and developing the Baylis-Hillman reaction as a useful and powerful tool in synthetic chemistry. [9][10][11][12][13][14][15][16][17][18][19][20][21] We have in fact, contributed significantly to its growth with respect to all the three essential components.

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“…In fact, is already well established in the literature that indolizines are synthesized at high temperatures. 29 We presented in Scheme 4 a short proposal of mechanism reaction for the 28 formation.As expected, the MAG 11 could be prepared in good yield without byproducts formations by decreasing the temperature at 60 o C (entry 8, Table 4). Then, it is clear that in lower temperature the addition of less nucleophilic t-butanol solvent on 25 do not occurs and also the formation of indolizines was not observed.…”

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confidence: 99%

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confidence: 99%

Microwave-promoted morita-baylis-hillman reactions: efficient synthesis of new monoacylglycerols (MAGs) as potential anti-parasitic compounds

Sousa¹,

G.L.²,

Silva³

et al. 2011

J. Braz. Chem. Soc.

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Descrevemos neste artigo, a irradiação por microondas promovendo a síntese de monoacilglicerol hidrofílico, MAG, a partir da hidrólise de um acrilato (15 min, 100%). Depois, o MAG foi transformado em adutos de Morita-Baylis-Hillman (AMBH) hidrofílicos, (54-82%, caminho 1). No caminho 2, outros AMBHs foram preparados em altos rendimentos (90-100%) e transformados em AMBH hidrofílicos em 70-90%. Durante e síntese em alta temperatura do AMBH, foi detectado por CG-EM a formação de uma indolizina inédita. Todos estes resultados estão de acordo com o novo mecanismo unificado para a reação de Morita-Baylis-Hillman. Estes novos monoacilgliceróis, bem como seus precursores sintéticos, são novos compostos antiparasitários em potencial.In this article we describe microwave irradiation promoting the synthesis of a hydrophilic monoacylglycerol, MAG, by hydrolysis of acrylate (15 min, 100%). After, MAG was transformed in hydrophilic Morita-Baylis-Hillman adducts (MBHA), (54-82%, pathway 1). In pathway 2, the different lipophilic MBHAs were prepared in high yields (90-100%) and transformed on hydrophilic MBHA, in 70-90%. Through the high temperature synthesis of one MBHA, a unprecedented indolizine formation was detected by GC-MS,. All results are in agreement with the new unified mechanism to the Morita-Baylis-Hillman reaction. These new monoacylglycerols, as well the its synthetic precursors, are new potential antiparasitic compounds.Keywords: Morita-Baylis-Hillman reaction, microwaves, monoacylglycerols, acrylates, potential antiparasitic IntroductionThe Morita-Baylis-Hillman reaction (MBHR) is an important way for C-C bond formation.1,2 It involves the alkenes coupling containing electron-withdrawing groups (EWG) with aldehyde, ketones or imines, among others. Tertiary amines are used as nucleophilic catalysts on which 1,4-diazabicyclo [2.2.2]octane (DABCO) is the most widely used (Scheme 1). The Morita-Baylis-Hillman adducts (MBHA) have been extensively used as starting materials in organic synthesis for a variety of applications, many of which have biological activity.2 An inconvenience associated with this reaction is, in several examples, the long reaction times. There are reports of reactions that, last up to 65 days. 2 However, due to the synthetic utility of these MBHA adducts, several protocols have been described to Sousa et al. 1635 Vol. 22, No. 9, 2011 improve the reaction time and yields, such as the use of ultrasound, high pressures, use of ionic liquids, change of catalyst, change of solvents, microwaves irradiation, and several other experimental protocols. 2Despite the fact that this reaction has already more than 40 years of existence, 1 the debate on the exact mechanism of reaction is still highlighted in the scientific community. The first catalytic cycle suggested by Hill and Isaacs 3 is still accepted, but being the rate-determining step (RDS) it remains at the center of the scientific debate. For example, the nonprotic 4 and protic 5 currently accepted mechanisms suggested by McQuade and Aggarwal res...

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The Baylis-Hillman Bromides as Versatile Synthons: A Facile One-Pot Synthesis of Indolizine and Benzofused Indolizine Frameworks

Cited by 77 publications

References 0 publications

Recent advances in the synthesis of indolizines and their π-expanded analogues

Recent advances in the synthesis of indolizines and their π-expanded analogues

The Baylis-Hillman reaction: Our vision and experience

Microwave-promoted morita-baylis-hillman reactions: efficient synthesis of new monoacylglycerols (MAGs) as potential anti-parasitic compounds

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