ChemInform Abstract: Design and Synthesis of Novel and Potent Monoamine Oxidase Inhibitors.

Branca, Quirico; Jakob‐Roetne, Roland; Kettler, R.; Roever, S.; Scalone, Michelangelo

doi:10.1002/chin.199610322

Cited by 2 publications

(3 citation statements)

References 1 publication

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“…115 In light of these precedent examples, the synthesis of arylcyclopropanes through crosscoupling reactions involving cyclopropyltin reagents appears to be impractical. However, the following case illustrates that, under certain conditions, highly electron deficient aryl electrophiles can be competent partners in this coupling reaction.…”

Section: D) Stille Reaction Of Cyclopropyltin Reagentsmentioning

confidence: 99%

Arylcyclopropanes: Properties, Synthesis and Use in Medicinal Chemistry

Gagnon

Duplessis

Fader

2010

Organic Preparations and Procedures International

108

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Section: D) Stille Reaction Of Cyclopropyltin Reagentsmentioning

confidence: 99%

Arylcyclopropanes: Properties, Synthesis and Use in Medicinal Chemistry

Gagnon

Duplessis

Fader

2010

Organic Preparations and Procedures International

108

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“…Treatment of pyrroles 6a-g with hydrazine hydrate in methanol at room temperature 33 gave the corresponding deprotected amines 7a-g, which were characterized after transformation into the corresponding N-butoxycarbonyl derivatives 8a-g (Scheme 2 and Table 1). This approach was also used in the synthesis of pyrrolo [1,2-a] [1,4]benzodiazepines 11a-c. A solution of diketone 4b in benzene was refluxed with anilines 9a-c in the presence of catalytic amount of trichloroacetic acid to give the corresponding pyrroles 10a-c. On heating with ethanolic hydrazine hydrate, pyrroles 10a-c were transformed into the corresponding pyrrolo [1,2-a] [1,4] By using a similar procedure, we also prepared the pyrrolo [1,2-a]diazepine 14. The diketone 4b, on heating with b-glycine ethyl ester hydrochloride (12) in the presence of sodium acetate, gave the pyrrole 13, which on treatment with hydrazine hydrate in ethanol and N,N-dimethylformamide gave the required product 14 (Scheme 4).…”

Section: Scheme 1 Synthesis Of N-furfurylphthalimides 3 and 1-phthalimentioning

confidence: 99%

“…2-(Aminomethyl)pyrroles have a broad range of biological activities 1 and have been shown to be potential antiinflammatory, 2 analgesic, 3 antidepressant, 4 antipsychotic, 5 or antitumor agents. 6 2-(Aminomethyl)pyrroles have also been used in the treatment of attention-deficit hyperactive disorder; 7 they have also been used in the preparation of conformationally restricted peptidomimetics 8,9 and anionbinding receptors, 9,10 and for the synthesis of pyrrolodiazepines [11][12][13] and other bioactive molecules containing pyrrole units annulated to other heterocycles.…”

mentioning

confidence: 99%

Furan Ring Opening-Pyrrole Ring Closure: Simple Route to 5-Alkyl-2-(aminomethyl)pyrroles

Бутин¹,

Nevolina²,

Shcherbinin³

et al. 2010

Synthesis

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A simple route to 5-alkyl-2-(aminomethyl)pyrroles is proposed that is based on hydrolytic ring opening of 5-alkylfurfurylamines followed by pyrrole ring closure under Paal-Knorr conditions.2-(Aminomethyl)pyrroles have a broad range of biological activities 1 and have been shown to be potential antiinflammatory, 2 analgesic, 3 antidepressant, 4 antipsychotic, 5 or antitumor agents. 6 2-(Aminomethyl)pyrroles have also been used in the treatment of attention-deficit hyperactive disorder; 7 they have also been used in the preparation of conformationally restricted peptidomimetics 8,9 and anionbinding receptors, 9,10 and for the synthesis of pyrrolodiazepines 11-13 and other bioactive molecules containing pyrrole units annulated to other heterocycles. 1i,13-15 The 2-(aminomethyl)pyrrole moiety is present in a variety of natural compounds such as porphobilinogen, an important intermediate in the biosynthesis of porphyrins, corrins, and chlorophylls. 16 2-(Aminomethyl)pyrroles can be transformed into porphyrinogens, 17 pyrrodimethanes, 18 porphyrins, or porphocyanins. 19 2-(Aminomethyl)pyrroles are usually synthesized by the reduction of the corresponding oximes, 1b,g,6a,9,10,20 nitriles, 1e,6a,19c,20b,21 azides, 1d,8b,12,14,22 or amides. 5a Other approaches to 2-(aminomethyl)pyrroles include the reductive amination of pyrrole-2-carbaldehydes, 8d,23 the transformation of pyrrole-2-carbaldehydes into imines followed by addition of nucleophilic reagents, 24 aminoalkylation of pyrroles, 22b,25 nucleophilic substitution of bromine in 2-(bromomethyl)pyrroles, 5a,18a,26 and a variety of intramolecular condensation reactions. 8g,27 One of the oldest and best-known methods for the synthesis of pyrroles is the Paal-Knorr reaction, i.e., the reaction of 1,4-diketones or their analogues with primary amines or ammonia. 28 However, the application of this approach to the synthesis of 2-(aminomethyl)pyrroles is very restricted, 1i,11,13 because of difficulties in preparing the necessary 1,4-diketones. 1-Phthalimido-2,5-diketones have been synthesized by a benzoin condensation-like addition of aldehydes to vinyl ketones in the presence of thiazolium salts as catalysts, 29 or by a three-step transformation of 2-(phthalimidomethyl)furans through formation of the corresponding 2,5-dimethoxy-2,5-dihydrofurans, ring opening, and double-bond hydrogenation. 11 An alternative route to these aminodiketones involves the reaction of N-(tert-butoxycarbonyl)glycine with potassium ethyl malonate followed by alkylation of the intermediate with a bromomethyl ketone. 1i 1,4-Diketones can also be prepared by acid-catalyzed cleavage of a furan ring. 30 When the starting furan contains a substituent that is appropriate for further transformation into an aminoalkyl group, a common sequence that involves cleavage of the furan ring followed by closure of the pyrrole ring can be used to provide an efficient synthesis of 2-(aminomethyl)pyrroles. Here, we describe an application of this approach to the transformation of 5-alkylfurfurylamines into the c...

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ChemInform Abstract: Design and Synthesis of Novel and Potent Monoamine Oxidase Inhibitors.

Cited by 2 publications

References 1 publication

Arylcyclopropanes: Properties, Synthesis and Use in Medicinal Chemistry

Arylcyclopropanes: Properties, Synthesis and Use in Medicinal Chemistry

Furan Ring Opening-Pyrrole Ring Closure: Simple Route to 5-Alkyl-2-(aminomethyl)pyrroles

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