Modern Amination Reactions

Kienle, Marcel; Dubbaka, Srinivas Reddy; Brade, Katja; Knöchel, Paul

doi:10.1002/chin.200748232

Cited by 3 publications

(3 citation statements)

References 1 publication

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“…This approach consists of two consecutive Pd-catalyzed reactions -a selective Buchwald-Hartwig [58][59][60][61][62][63] reaction of 2chloroaniline 34 with 4-chloroquinoline 33 followed by an intramolecular arylation [64][65][66] of the resulting compound 35 to afford the 11H-indolo[3,2-c]quinoline 16.…”

Section: Palladium-catalyzed Coupling Reactionmentioning

confidence: 99%

Isolation, Biological Activities and Synthesis of Indoloquinoline Alkaloids: Cryptolepine, Isocryptolepine and Neocryptolepine

Parvatkar¹,

Parameswaran²,

Tilve

2011

COC

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The tetracyclic heteroaromatic compounds cryptolepine, isocryptolepine and neocryptolepine are all naturally occurring indoloquinoline alkaloids isolated from the shrub Cryptolepis sanguinolenta and are important due to their wide spectrum of biological properties. This review describes the isolation, brief biological activities and various synthetic methodologies developed during recent years for the preparation of this important class of alkaloids, with special emphasis on preparation and properties of cryptolepine 1, isocryptolepine 2 and neocryptolepine 3.Pd 2 (dba) 3 (2.5 mol%), P(tBu) 3 (10 mol%) K 3 PO 4 , dioxane pressure tube 120 0 C, 3h, 95% CH 3 I, DMF, 80 0 C, 1 h r.t., overnight 75% 33 34 35 16 2 Scheme 7.

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Section: Palladium-catalyzed Coupling Reactionmentioning

confidence: 99%

Isolation, Biological Activities and Synthesis of Indoloquinoline Alkaloids: Cryptolepine, Isocryptolepine and Neocryptolepine

Parvatkar¹,

Parameswaran²,

Tilve

2011

COC

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“…The chemical process in which a nucleophile (Nu -) attacks an electrophilic nitrogen atom of σ+ NH-O-EWG σ-and leads to the Nu-NH 2 product with simultaneous liberation of the O-EWG -leaving group is usually named electrophilic amination [15][16][17]. The examples of reagents that comprise the electrophilic nitrogen atom and a good leaving group include: hydroxylamine-O-sulfonic acid (HOSA) [18], O-alkyl- [19], O-aryl- [20], O-acyl- [21], O-phosphinyl- [22], O-silyl- [23], O-sulfonyl-hydroxylamines [24], their oximes, and oxaziridines [25] (compounds A, B, and C in Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and reactivity of heterocyclic hydroxylamine-O-sulfonates

Sączewski

Korcz

2014

Heterocyclic Communications

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The heterocyclic hydroxylamine-O-sulfonates constitute a novel family of formal O-substituted hydroxyguanidines and hydroxyamidines that serve as functional precursors to a variety of fused heterocyclic ring systems incorporating N-N, N-O, N-S, or N-N + moiety. They are readily accessible from the reaction of 2-chloroazoles, 2-chloroazines, and 2-chlorodiazines with hydroxylamine-O-sulfonic acid. They have a rich chemistry exemplified by tandem reactions, such as nucleophilic addition-electrophilic amination, nucleophilic addition-electrophilic 5-endo-trig cyclization or fluorogenic Mannich-electrophilic amination reaction. The heterocyclic hydroxylamine-O-sulfonates have significant potential for use in synthesis of anticancer, antiviral, and antimicrobial agents. The newly discovered fluorogenic reaction and fluorescent dyes (Safirinium-P and Safirinium-Q) have found applications in fluorescent detection and labeling.

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“…Uma outro alternativa ao uso de metais de transição, porém não muito utilizada devido as suas limitações, é a síntese de diarilamina utilizando reagentes de Grignard e compostos nitroaromáticos (Kienle et al, 2007).…”

Section: Fumagalli F Introduçãounclassified

Química de alcaloides carbazólicos: síntese de Claurailas e de biblioteca de análogos estruturais

Fumagalli¹

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Modern Amination Reactions

Cited by 3 publications

References 1 publication

Isolation, Biological Activities and Synthesis of Indoloquinoline Alkaloids: Cryptolepine, Isocryptolepine and Neocryptolepine

Isolation, Biological Activities and Synthesis of Indoloquinoline Alkaloids: Cryptolepine, Isocryptolepine and Neocryptolepine

Synthesis and reactivity of heterocyclic hydroxylamine-O-sulfonates

Química de alcaloides carbazólicos: síntese de Claurailas e de biblioteca de análogos estruturais

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