A study of the reaction of N-chlorosuccinimide with indoles and its analytical application

Islam, Imadul; Misra, D.D.; Singh, Reena; Sharma, J. P.

doi:10.1016/0039-9140(84)80189-7

Cited by 4 publications

(2 citation statements)

References 4 publications

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“…There are several colorimetric methods available for indole anal-ysis, wherein indole is derivatized into a variety of colored products. Derivatizing agents include phosphoric acid (Boctor 1972;Patterson 1948), chloranil (Manzar and Fasihullah 1988), lignine (Davidson and others 1973), electron acceptor molecules (Hutzinger 1969;Hutzinger and others 1972), sodium nitroprusside (Sugumaran and Vaidyanathan 1978), sodium nitrite-glycine-HCl (Boctor and others 1978), halosuccinimides (Islam andothers 1984), haloacetamides (Gopal andothers 1977), and most importantly, 4-(dimethylamino) benzaldehyde (Duggan and Strausberger 1946;Anthony and Street 1970;Ehmann 1977;Cheuk and Finne 1981;Veveris and others 1988;Tantillo and others 1996). Several versions of the 4-(dimethylamino)benzaldehyde (DMAB) derivatization of indole in shrimp have been reported in the literature, but each method involves tedious multi-step procedures that extract indole from shrimp tissue.…”

Section: S Eafood Continues To Grow In Popularity In the Americanmentioning

confidence: 99%

Rapid Colorimetric Method to Detect Indole in Shrimp with Gas Chromatography Mass Spectrometry Confirmation

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Takenaka

Kim-Hayes

et al. 2003

Journal of Food Science

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With increased public concern over the freshness and quality of seafood, more pressure is being applied to the industry to provide better products in the market place. Simple, fast, and inexpensive tests are needed to assess seafood quality. Seafood decomposition can be characterized by biogenic amine formation, such as the formation of indole in shrimp. We have developed a rapid colorimetric method using 4-(dimethylamino)benzaldehyde method that detects indole in decomposing shrimp. This method, as well as the confirmatory gas chromatography/mass spectrometry (GC/MS) method, is centered on a simple toluene extraction technique that recovers indole with high efficiency. Excellent agreement was obtained between the colorimetric and GC/MS quantitative results for shrimp decomposition.

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Section: S Eafood Continues To Grow In Popularity In the Americanmentioning

confidence: 99%

Rapid Colorimetric Method to Detect Indole in Shrimp with Gas Chromatography Mass Spectrometry Confirmation

Snellings

Takenaka

Kim-Hayes

et al. 2003

Journal of Food Science

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“…Furthermore, the stabilizing hydrogen-bonding interactions between the nitro group and the hydroxyl group would also favor intermediate 21a . Much to our delight, treatment of N -chlorosuccinimide (NCS) and water allowed for the formation of oxindole through hydrolysis of the corresponding 2-chloroindole, which underwent a concomitant aldol cyclization to exclusively produce oxabicyclo[3.3.1]nonane 17 as a single isomer in 90% yield. To the best of our knowledge, this oxidation/cyclization cascade reaction represents one of the few examples of a ketone aldol reaction of 3-substituted oxindoles .…”

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confidence: 99%

Divergent Entry to Gelsedine-Type Alkaloids: Total Syntheses of (−)-Gelsedilam, (−)-Gelsenicine, (−)-Gelsedine, and (−)-Gelsemoxonine

Wang

Gao

2018

J. Am. Chem. Soc.

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The gelsedine-type alkaloids possess a common oxabicyclo[3.2.2]nonane core and spiro- N-methoxyindolinone moiety along with a diversely functionalized heterocycle embedded in the compact framework. Herein we disclose a divergent entry to gelsedine-type alkaloids that hinges on rapid assembly of the common core by the orchestrated application of an asymmetric Michael addition, a tandem oxidation/aldol cyclization, and a pinacol rearrangement and generation of the structural diversity via a late-stage heterocyclization. The power of this strategy has been demonstrated through very short total syntheses of four gelsedine-type alkaloids: gelsedilam, gelsenicine, gelsedine, and gelsemoxonine.

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On the synthesis and isolation of chlorocarbazoles obtained by chlorination of carbazoles

Bonesi

Erra‐Balsells

1997

Journal of Heterocyclic Chem

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Carbazole (1) undergoes electrophilic aromatic substitution with various chlorinating reagents. Although 3‐chlorocarbazole (1b), 3,6‐dichlorocarbazole (1d) and 1,3,6,8‐tetrachlorocarbazole (1f) obtained by chlorination of carbazole were isolated and characterized sometime ago, 1‐chlorocarbazole (1a), 1,6‐dichlorocarbazole (1c) and 1,3,6‐trichlorocarbazole (1e) had never been isolated from the reaction mixtures. The preparation and subsequent isolation and characterization of 1a, 1b, 1c, 1d, 1e and 1f are reported (mp, tR, Rf, 1H‐ and 13C‐nmr, ms). Physical and spectroscopic properties of 1c are compared with those of 1b and 1d in order to show that the former is the major product obtained in several chlorinating processes. As chlorinating reagents, chlorine in glacial acetic acid, sulfuryl chloride, N‐chlorosuccinimide, N‐chlorosuccinimide‐silica gel, N‐chlorobenzotriazole, and N‐chlorobenzotriazole‐silica gel in dichloromethane and in chloroform have been used and their uses have been compared. The chlorination reaction of different carbazole derivatives such as 2‐hydroxycarbazole (2), 2‐acetoxycarbazole (3), 3‐bromocarbazole (4) and 3‐nitrocarbazole (5) was also studied and the corresponding chloro derivatives 2a, 2b, 2c, 2d, 3a, 3b, 3c, 3d, 3e, 3f, 4a, 4b, 4c, 4d, 5a and 5b are described for the first time. Semiempirical PM3 calculations have been performed in order to predict reactivity of carbazole (1), substituted carbazoles 2–5 and chlorocarbazoles (Scheme 1). Theoretical and experimental results are discussed briefly.

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A study of the reaction of N-chlorosuccinimide with indoles and its analytical application

Cited by 4 publications

References 4 publications

Rapid Colorimetric Method to Detect Indole in Shrimp with Gas Chromatography Mass Spectrometry Confirmation

Rapid Colorimetric Method to Detect Indole in Shrimp with Gas Chromatography Mass Spectrometry Confirmation

Divergent Entry to Gelsedine-Type Alkaloids: Total Syntheses of (−)-Gelsedilam, (−)-Gelsenicine, (−)-Gelsedine, and (−)-Gelsemoxonine

On the synthesis and isolation of chlorocarbazoles obtained by chlorination of carbazoles

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