Comparative studies for selective deprotection of the N-arylideneamino moiety from heterocyclic amides: kinetic and theoretical studies

George, Bobby J.; Dib, Hicham H.; Abdallah, Mariam R.; Ibrahim, Maher R.; Khalil, Nasser S. A. M.; Ibrahim, Yehia A.; Al‐Awadi, Nouria A.

doi:10.1016/j.tet.2005.10.069

Cited by 12 publications

(1 citation statement)

References 25 publications

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“…Earlier, we have used N ‐substituted cyclic amides, thioamides, and related nitrogen heterocycles as substrates in thermal gas‐phase elimination reactions to prepare condensed heterocyclic compounds. These reactions were found to proceed via a six‐membered transition state (TS) with elimination of arylnitriles, and with rates and products of reaction being affected by structural factors and by the nature of the heterocyclic ring . Here, we report the results of a mechanistic investigation of the FVP and STP reactions of substituted N ‐arylidine‐ N′ ‐pyrimidin‐2‐yl‐hydrazines 1a , 1b , 1c , 1d , 1e in which the arylidenediaza substituent is on a ring carbon atom of the nitrogen heterocycle.…”

Section: Introductionmentioning

confidence: 89%

Product and Mechanism of Gas-phase Pyrolysis of 2-arylidinehydrazinopyrimidines: Interesting Route to Condensed Heterocycles[1]

Al-Awadi

Ibrahim

El‐Dusouqui

et al. 2014

J. Heterocyclic Chem.

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in Wiley Online Library (wileyonlinelibrary.com).Gas-phase pyrolysis of N-arylidine-N′-pyrimidin-2-yl-hydrazine derivatives 1a-e gave the corresponding arylnitriles 2a-e, 2-aminopyrimidine 3, 3-phenyl-1,2,4-triazolo[4,3-a]pyrimidines 4, 2-phenyl-1,2,4-triazolo [1,5-a]pyrimidines 5, 2,4,5-triphenyl-1H-imidazole 6, and 2,3-diphenylquinoline 7. The analyses of the reaction products are reported and used to elucidate the mechanism of the pyrolytic process.

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Section: Introductionmentioning

confidence: 89%

Product and Mechanism of Gas-phase Pyrolysis of 2-arylidinehydrazinopyrimidines: Interesting Route to Condensed Heterocycles[1]

Al-Awadi

Ibrahim

El‐Dusouqui

et al. 2014

J. Heterocyclic Chem.

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Protection for the Amino Group

Wuts

Greene²

2006

Greene's Protective Groups in Organic Synthesis

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Protection for the Amino Group

2014

Greene's Protective Groups in Organic Synthesis

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CARBAMATES 907Carbamate Derived from an Amine and CO 2 , 908 Methyl and Ethyl, 909 9-Fluorenylmethyl, 912 2,6-Di-t-butyl-9-fluorenylmethyl, 915 2,7-Bis (trimethylsilyl)fluorenylmethyl, 915 2-(2-Ethylhexyl)-9-fluorenylmethyl, 915 2,7-Bis-(2-ethylhexyl)-9-fluorenylmethyl, 915 9-(2-Sulfo)fluorenylmethyl, 916 9-(2,7-Dibromo)fluorenylmethyl, 916 17-Tetrabenzo[a,c,g,i]fluorenylmethyl, 916 2-Chloro-3-indenylmethyl, 916 Benz[f]inden-3-ylmethyl, 916 1,1-Dioxobenzo[b]thiophene-2-ylmethyl, 917 2,7-Di-t-butyl[9-(10,10-dioxo-10,10,10,10-tetrahydrothioxanthyl)]methyl, 917 Azidomethyl, 920 2-(Hydroxymethyl)-3-phenyl-4H-1-benzothiopyran-4-one 1,1-Dioxide, 920 2-Methylsulfonyl-3-phenyl-1-prop-2-enyloxy, 920 Substituted Ethyl Carbamates 921 2,2,2-Trichloroethyl, 921 2-Trimethylsilylethyl, 923 (2-Phenyl-2-trimethylsilyl)ethyl, 925 2-(Triphenylsilyl)ethyl, 925 2-Phenylethyl, 927 2-Chloroethyl, 927 2 3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decyl, 927 1,1-Dimethyl-2-haloethyl, 927 1,1-Dimethyl-2,2-dibromoethyl, 927 1,1-Dimethyl-2,2,2-trichloroethyl, 928 2-(2´and 4´-Pyridyl)ethyl, 928

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Comparative studies for selective deprotection of the N-arylideneamino moiety from heterocyclic amides: kinetic and theoretical studies

Cited by 12 publications

References 25 publications

Product and Mechanism of Gas-phase Pyrolysis of 2-arylidinehydrazinopyrimidines: Interesting Route to Condensed Heterocycles[1]

Product and Mechanism of Gas-phase Pyrolysis of 2-arylidinehydrazinopyrimidines: Interesting Route to Condensed Heterocycles[1]

Protection for the Amino Group

Protection for the Amino Group

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