One-pot Graebe-Ullmann synthesis of γ-carbolines under microwave irradiation

Molina, A.; Vaquero, Juan J.; Garcia‐Navio, J. L.; Alvárez‐Builla, Julio

doi:10.1016/s0040-4039(00)77653-2

Cited by 59 publications

(28 citation statements)

References 12 publications

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“…It has been reported that certain reactions such as Diels-Alder [15,16], ethenoid [17], Claisen reaction [18], Fischer cyclization [19], synthesis of heterocycles [20], hydrolysis of esters [21,22], phosphoanhydride [23] and adenosine triphosphate formation [24], rapid hydrogenation [25], deprotection of benzyl esters [26], deacetylation of diacetates [27], Graebe-Ullmann synthesis [28], oxazoline formation [29,30], Knoevengel condensation [31], and aromatic ether formation [32,33] could be facilitated by microwave irradiation. However, to the best of our knowledge, no such application has been devised for the previously described Mannich-type reaction.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of cyclic esters of N-toluenesulfonyl ?-aminophosphonic acid

Dai

Chen

1998

Heteroatom Chem.

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Section: Resultsmentioning

confidence: 99%

Synthesis of cyclic esters of N-toluenesulfonyl ?-aminophosphonic acid

Dai

Chen

1998

Heteroatom Chem.

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“…An alternative method for synthesizing g-carbolines is the Graebe-Ullmann reaction, which consists of the preparation of substituted 4-pyridylbenzotriazoles or 1-phenyltriazolo [4,5-c]pyridines and their further thermal decomposition [84,85], microwave irradiation [86], photolysis [87], or heating in phosphoric [88,89] or polyphosphoric [86, 90 -96] acids.…”

Section: Graebe-ullmann Reactionmentioning

confidence: 99%

Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

Smirnova¹,

Golovko²,

Граник³

2011

Pharm Chem J

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The main trends in the development of the chemistry of a-, g-, and d-carbolines are generalized. Syntheses of carbolines based on pyridine derivatives (including the Fischer synthesis, Graebe-Ullmann reaction, thermal decomposition of azides, photochemical cyclization of anilinopyridines, arylation of substituted pyridines and piperidones, etc.) and based on indole derivatives are described. Published data about the biological activity of compounds belonging to these series are summarized.Four classes of pyridoindoles, i.e., carbolines (1 -4), are known. Of these, b-carbolines (2) have been studied most completely. Numerous studies, including several reviews [1 -3], have addressed the synthesis and various properties of this class of compounds. The properties of the other carbolines have been studied in less detail, e.g., their syntheses and chemical and physicochemical properties have not yet been discussed and compared in the literature.A detailed comparison seems especially important because precisely such an analysis can expose the basic features that make these classes chemically and biologically significant. This is especially important during research directed at the discovery of new biologically active compounds. Because the large volume of literature dedicated to b-carbolines makes it practically impossible to discuss it in a single review, the present review is limited to a comparison of the other carbolines only, the syntheses of which have been discussed much less in the literature. We intend to discuss the main trends in the development of the chemistry of a-, g-, and d-carbolines without pretending to include all literature in its entirety in order to compare the potential of finding novel effective drugs in these series. We discuss first reviews dedicated to pyridoindoles [2 -5], including a rather recent review of g-carbolines [6]. Then we switch to chemical approaches to the synthesis of selected carboline derivatives, noting briefly publications on their biological properties.Pyridoindoles (carbolines), including pyrido[4,3-b]indoles (g-carbolines), some of which exhibit a broad spectrum of biological activity, are definitely interesting. Drugs of this class already exist, e.g., neuroleptic carbidine 5 (Carbidinum or Stobadine) and dimebon antihistamine drugs 6 (Dimebonum) and diazoline 7 (Diazolinum or Omeril) [7,8]. Furthermore, dimebon exhibited pronounced anti-NMDA (N-methyl-D-asparate, ED 50 = 42 mg/kg i.p.) and anticalcium activity (blocks calcium channels, IC 50 = 57 mM) and inhibited acetylcholinesterase (ACE) and butyrylcholinesterase (BuCE) (IC 50 = 42 and 7.9 mM, respectively) in in vitro tests. It also had pronounced cognitive-stimulant properties in in vivo tests for a neurotoxic 654 0091-150X/11/4412-0654

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“…Reaction of pyridinium N-dicyanomethylide with ethyl phenylpropiolate or phenylacetylene gave the possible regioisomers 13 20 . Reaction of 4-chloroazines with benzotriazoles gave the triazole derivatives 14, and 2-amino-pyridines with 2-naphthaldehyde or pyridine-2-aldehyde and isocyanide afforded the imidazo[1,2-a]pyridines 15 21,22 . Oxazolopyridines 16 were obtained by intramolecular cyclization of hydroxyamidines 23 .…”

Section: Heterocycles With One Heteroatommentioning

confidence: 99%

Account of microwave irradiation for accelerating organic reactions

Ashry¹,

Kassem²

2005

Arkivoc

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This account provides a summary of a chapter on Microwave Irradiation for Accelerating Organic Reactions in Advances in Heterocyclic Chemistry, volume 90, Part II: Six, Sevenmembered, Spiro and Fused Heterocycles by E. S. H. El Ashry, A. A. Kassem and E. Ramadan. Microwave irradiation (MWI) has been used extensively in organic synthesis. Application of MWI leads to many advantages, like the use of non-corrosive and inexpensive reagents, in addition to the eco-friendly "green chemistry" economical and environmental impacts.

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One-pot Graebe-Ullmann synthesis of γ-carbolines under microwave irradiation

Cited by 59 publications

References 12 publications

Synthesis of cyclic esters of N-toluenesulfonyl ?-aminophosphonic acid

Synthesis of cyclic esters of N-toluenesulfonyl ?-aminophosphonic acid

Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

Account of microwave irradiation for accelerating organic reactions

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