Collect. Czech. Chem. Commun. 1988, 53, 601-618
https://doi.org/10.1135/cccc19880601

Base-catalyzed formation of spiro adduct from N-methyl-N-(2,4,6-trinitrophenyl)glycinamide, the smiles rearrangement of the amide in methanol

Jaromír Kaválek, Vladimír Macháček, Makky M. M. Hassanien and Vojeslav Štěrba

Department of Organic Chemistry, Institute of Chemical Technology, 532 10 Pardubice

Individual author index pages


Other CCCC articles of these authors

  • Jiří Hanusek* and Vladimír Macháček
    Intramolecular base-catalyzed reactions involving interaction between benzene nitro groups and ortho carbon chains
    2009, Vol. 74, Issue 5, pp. 811–833 [Abstract]
  • Jiří Hanusek*, Miloš Sedlák, Roman Keder and Vojeslav Štěrba
    Kinetics and Mechanism of Desulfurization Reaction of 1-Methyl-2-phenylquinazoline-4(1H)-thiones
    2004, Vol. 69, Issue 12, pp. 2212–2222 [Abstract]
  • Jaromír Mindl*, Oldřich Hrabík, Vojeslav Štěrba and Jaromír Kaválek
    Cyclization of Substituted Phenyl N-(2-Hydroxybenzyl)carbamates in Aprotic Solvents. Synthesis of 4H-1,3-Benzoxazin-2(3H)-ones
    2000, Vol. 65, Issue 8, pp. 1262–1272 [Abstract]
  • Jaromír Mindl*, Jaromír Kaválek, Helena Straková and Vojeslav Štěrba
    Kinetics of Base-Catalysed Hydrolysis and Cyclisation of Substituted Acetamide and Benzamide O-(Phenoxycarbonyl)oximes
    1999, Vol. 64, Issue 10, pp. 1641–1653 [Abstract]
  • Miloš Sedlák, Jiří Hanusek, Radim Bína, Jaromír Kaválek and Vladimír Macháček*
    Kinetics and Mechanism of the Formation and Decomposition of Imidazolin-4-ones from 2-(N-Benzoylamino)alkanamides in Aqueous Medium
    1999, Vol. 64, Issue 10, pp. 1629–1640 [Abstract]
  • Libor Dušek*, Jaromír Kaválek and Vojeslav Štěrba
    Kinetics of Methanolysis of Substituted Benzamide O-(Phenoxycarbonyl)- and O-(Alkoxycarbonyl)oximes Catalyzed by Sodium Methanolate
    1999, Vol. 64, Issue 2, pp. 265–287 [Abstract]
  • Miloš Sedlák, Jaromír Kaválek, Petr Mitaš and Vladimír Macháček
    Kinetics and Mechanism of Cyclization of Substituted 2-(Benzoylamino)alkanamides in Strongly Basic Medium
    1998, Vol. 63, Issue 3, pp. 394–406 [Abstract]
  • Petr Mitaš, Miloš Sedlák and Jaromír Kaválek
    Substituent Effect on Acidity of Substituted 2-(4-Nitrobenzoylamino)alkanamides in Methanol-Dimethyl Sulfoxide Mixtures
    1998, Vol. 63, Issue 1, pp. 85–93 [Abstract]
  • Petr Mitaš, Jaromír Kaválek and Oldřich Pytela
    Dissociation of Amides in Strongly Basic Medium of Sodium Methoxide in Dimethyl Sulfoxide-Methanol Mixtures
    1997, Vol. 62, Issue 10, pp. 1562–1576 [Abstract]
  • Marek Janík, Vladimír Macháček and Oldřich Pytela
    Kinetics of Cyclization of Methyl S-(2,4,6-Trinitrophenyl)mercaptoacetate to 2-Methoxycarbonyl-5,7-dinitrobenzo[d]thiazol-3-oxide
    1997, Vol. 62, Issue 9, pp. 1429–1445 [Abstract]
  • Jaroslava Horáčková and Vojeslav Štěrba
    Kinetics of Coupling of 4-Methoxybenzenediazonium Ion with 2,6-Dihydroxypyridine
    1996, Vol. 61, Issue 6, pp. 951–956 [Abstract]
  • Miloš Sedlák, Aleš Halama, Jaromír Kaválek, Vladimír Macháček, Petr Mitaš and Vojeslav Štěrba
    Preparation and NMR Spectra of Substituted 2-(4-Nitrophenyl)imidazolinones
    1996, Vol. 61, Issue 6, pp. 910–920 [Abstract]
  • Vladimír Macháček, Alexandr Čegan, Aleš Halama, Olga Rožňavská and Vojeslav Štěrba
    Reactions of 4-Amino-3-penten-2-one and Its NSubstituted Derivatives with Diazonium Ions
    1995, Vol. 60, Issue 8, pp. 1367–1379 [Abstract]
  • Miloš Sedlák, Aleš Halama, Jaromír Kaválek, Vladimír Macháček and Vojeslav Štěrba
    Preparation, 1H and 13C NMR Spectra of Substituted 2-Benzoylaminocarboxamides
    1995, Vol. 60, Issue 1, pp. 150–160 [Abstract]
  • Vladimír Macháček, Jana Manová, Miloš Sedlák and Vojeslav Štěrba
    Kinetics and Mechanism of Reaction of 2,4-Dinitrobenzaldehyde with Hydroxide Ion
    1994, Vol. 59, Issue 10, pp. 2262–2268 [Abstract]
  • Jaromír Kaválek, Vladimír Macháček and Vojeslav Štěrba
    Coupling Kinetics of 4-Sulfobenzenediazonium Ion with 2,4-Thiazolidinedione, Its 3-Methyl Derivative and 3-Methyl-5-isoxazolone
    1994, Vol. 59, Issue 9, pp. 2022–2028 [Abstract]
  • Jaroslava Horáčková and Vojeslav Štěrba
    Kinetics of Substitution of 4-Methoxyphenylazo Groups of 2,6-Dioxo-5(3)-(4-methoxyphenylazo)-3(5)-(4-methoxyphenylhydrazono)-1,2,3,6-tetrahydropyridine-4-carboxylic Acid by Reaction with 4-Nitrobenzenediazonium Cation
    1994, Vol. 59, Issue 7, pp. 1665–1672 [Abstract]
  • Jaromír Kaválek, Vladimír Macháček, Miloš Sedlák and Vojeslav Štěrba
    Study of Cyclization of 1-Benzoyl-3-methyl-3-(2-methoxycarbonylphenyl)thiourea to 1-Methyl-2-thioxo-4-quinazolone
    1993, Vol. 58, Issue 5, pp. 1122–1132 [Abstract]
  • Jaroslava Horáčková and Vojeslav Štěrba
    Coupling Kinetics of Benzenediazonium Ions with 2,6-Dioxo-3-(p-substituted phenylhydrazono)-1,2,3,6-tetrahydropyridine-4-carboxylic Acid
    1992, Vol. 57, Issue 9, pp. 1915–1927 [Abstract]
  • Jaromír Kaválek, Vladimír Macháček, Miloš Sedlák and Vojeslav Štěrba
    Kinetics and Mechanism of Cyclization of N-(2-Methoxycarbonylphenyl)-N-methylsulfonamide to 1-Methyl-(1H)-2,1,3-benzothiadiazine-4(3H)-one-2,2-dioxide
    1992, Vol. 57, Issue 6, pp. 1282–1290 [Abstract]
  • Jaromír Kaválek, Vladimír Macháček, Miloš Sedlák and Vojeslav Štěrba
    Kinetics and mechanism of cyclization of N-(2-methoxycarbonylphenyl)-N’-methylsulphonamide to 3-methyl-(1H)-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide
    1991, Vol. 56, Issue 8, pp. 1701–1710 [Abstract]
  • Jaroslava Horáčková, Jaromír Kaválek, Jiří Kulič and Vojeslav Štěrba
    Azo coupling kinetics of benzenediazonium ions with citrazinic acid
    1991, Vol. 56, Issue 2, pp. 386–397 [Abstract]
  • Oldřich Pytela, Taťjana Nevěčná and Jaromír Kaválek
    Reactivity of proton and general acid with 1,3-bis-(4-methylphenyl)triazene in aqueous methanol
    1990, Vol. 55, Issue 11, pp. 2701–2706 [Abstract]
  • Jiří Klicnar, Jaromír Mindl and Vojeslav Štěrba
    Kinetics of reaction of 1,2-diaminobenzene with phenylglyoxal
    1990, Vol. 55, Issue 5, pp. 1216–1222 [Abstract]
  • Jaromír Kaválek, Ulrika Králíková, Vladimír Macháček, Miloš Sedlák and Vojeslav Štěrba
    Kinetics and mechanism of solvolysis of N-aryl sulfuric diamides
    1990, Vol. 55, Issue 1, pp. 202–222 [Abstract]
  • Taťjana Nevěčná, Oldřich Pytela, Miroslav Ludwig and Jaromír Kaválek
    Solvent effects on kinetics and mechanism of acid-catalyzed decomposition of 1,3-bis(4-methylphenyl)triazene I. Reactions in alcohols
    1990, Vol. 55, Issue 1, pp. 147–155 [Abstract]
  • Vítězslav Zima, Oldřich Pytela, Jaromír Kaválek and Miroslav Večeřa
    Reactivity of nucleophiles in dimethyl sulfoxide and its comparison with nucleophilic reactivity in protic medium
    1989, Vol. 54, Issue 10, pp. 2715–2720 [Abstract]
  • Jaromír Kaválek, Lubomír Kacetl and Marcela Kaválková
    Kinetics of methanolysis of 1-(2-halogeno and 2,6-dihalogenobenzoyl)-3-(4-chlorophenyl)ureas
    1989, Vol. 54, Issue 5, pp. 1363–1369 [Abstract]
  • Jaromír Kaválek, Vladimír Macháček, Gabriela Svobodová and Vojeslav Štěrba
    Kinetics and mechanism of reversible, base-catalyzed ring closure of 3-(methoxycarbonyl)propionanilide and O-(methoxycarbonylmethyl)-N-phenylcarbamate
    1989, Vol. 54, Issue 4, pp. 1005–1011 [Abstract]
  • Vladimír Macháček, Alexandr Čegan, Miloš Sedlák and Vojeslav Štěrba
    Formation of spiro adduct from N-methyl-N-(2,4,6-trinitrophenyl)glycine anion
    1989, Vol. 54, Issue 2, pp. 440–445 [Abstract]
  • Vladimír Macháček, Miloslav Sebránek and Vojeslav Štěrba
    Reaction of N-methyl-N-(2,4-dinitrophenyl)glycine methylamide with methoxide
    1989, Vol. 54, Issue 2, pp. 430–439 [Abstract]
  • Jiří Klicnar, Jaromír Mindl, Ivana Obořilová, Jaroslav Petříček and Vojeslav Štěrba
    Reaction kinetics of 1,2-diaminobenzene with ethyl 2-oxopropanoate and 2,3-butanedione
    1988, Vol. 53, Issue 12, pp. 3154–3163 [Abstract]
  • Vladimír Macháček, Vojeslav Štěrba, Ivan Kolb and Antonín Lyčka
    Reactions of methyl esters of N-(2,4-dinitrophenyl)glycine and N-methyl-N-(2,4-dinitrophenyl)glycine with sodium methoxide
    1988, Vol. 53, Issue 5, pp. 1044–1052 [Abstract]
  • Jaromír Kaválek, Vladimír Macháček, Vojeslav Štěrba and Antonín Lyčka
    Formation of N-methyl-2-nitroso-4,6-dinitroaniline from methyl ester of N-methyl-N-(2,4,6-trinitrophenyl)glycine
    1988, Vol. 53, Issue 5, pp. 1033–1043 [Abstract]
  • Jaromír Kaválek, Josef Jirman, Vladimír Macháček and Vojeslav Štěrba
    The methanolysis kinetics and dissociation constants of 1-(subst. benzoyl)-3-phenylthioureas
    1988, Vol. 53, Issue 3, pp. 593–600 [Abstract]
  • Antonín Lyčka, Vladimír Macháček and Josef Jirman
    15N, 13C, and 1H NMR spectra of 1-substituted-2,4,6-trinitrobenzenes
    1987, Vol. 52, Issue 12, pp. 2946–2952 [Abstract]
  • Vladimír Macháček, Makky M. M. Hassanien and Vojeslav Štěrba
    Kinetics and mechanism of spiro adduct formation from and smiles rearrangement of N-methyl-N-(2,4,6-trinitrophenyl)aminoacetanilide. Base-catalyzed transformation of N-(2,4,6-trinitrophenylamino)acetanilide into 2-nitroso-4,6-dinitroaniline
    1987, Vol. 52, Issue 9, pp. 2225–2240 [Abstract]
  • Jaromír Kaválek, Vladimír Macháček, Gabriela Svobodová and Vojeslav Štěrba
    Kinetics of acid-catalyzed cyclization of substituted hydantoinamides to substituted hydantoins
    1987, Vol. 52, Issue 8, pp. 1999–2004 [Abstract]
  • Jaromír Kaválek, Josef Jirman, Vladimír Macháček and Vojeslav Štěrba
    An anomalous effect of methyl group on acidity of acylthioureas
    1987, Vol. 52, Issue 8, pp. 1992–1998 [Abstract]
  • Jaromír Kaválek, Ludmila Hejtmánková and Vojeslav Štěrba
    Kinetics and mechanism of solvolysis of substituted phenyl N-phenylbenzimidoesters
    1987, Vol. 52, Issue 5, pp. 1285–1297 [Abstract]
  • Jaromír Mindl and Vojeslav Štěrba
    Mechanism of base-catalyzed cyclization of ethyl N-(substituted aminocarbonyl)glycinates
    1987, Vol. 52, Issue 1, pp. 156–161 [Abstract]
  • Vladimír Macháček, Gabriela Svobodová and Vojeslav Štěrba
    Kinetics and mechanism of base-catalyzed cyclization of substituted amides and nitriles of hydantoic acid
    1987, Vol. 52, Issue 1, pp. 140–155 [Abstract]
  • Vladimír Macháček, Vojeslav Štěrba and Antonín Lyčka
    Mechanism of the reaction of 1-methoxy- and 1-chloro-2,4,6-trinitrobenzene with dimethyl malonate anion
    1987, Vol. 52, Issue 1, pp. 132–139 [Abstract]
  • Jaromír Kaválek, Josef Jirman and Vojeslav Štěrba
    Reactions of 1,3-diacylthioureas with methoxide ion and with amines
    1987, Vol. 52, Issue 1, pp. 120–131 [Abstract]
  • Vladimír Macháček, Makky M. M. Hassanien, Vojeslav Štěrba and Antonín Lyčka
    Formation of the Meisenheimer spiro adduct of N-(2,4,6-trinitrophenyl)alanine methylamide and its rearrangement to 2-amino-N-methyl-N-(2,4,6-trinitrophenyl)propanamide
    1986, Vol. 51, Issue 9, pp. 1972–1985 [Abstract]
  • Jaromír Kaválek, Josef Panchartek, Tomáš Potěšil and Vojeslav Štěrba
    Kinetics of the reaction of guanyl-O-methylisourea hydrochloride with dimethylformamide dimethylacetal
    1986, Vol. 51, Issue 9, pp. 1964–1971 [Abstract]
  • Jaromír Kaválek, Josef Panchartek, Tomáš Potěšil and Vojeslav Štěrba
    Solvolysis kinetics of ethyl 3-ethoxy-3-iminopropanoate
    1986, Vol. 51, Issue 3, pp. 677–683 [Abstract]
  • Jaromír Kaválek, Vladimír Macháček, Gabriela Svobodová and Vojeslav Štěrba
    Base catalyzed cyclization of substituted esters of hydantoic and thiohydantoic acids
    1986, Vol. 51, Issue 2, pp. 375–390 [Abstract]
  • Vladimír Macháček, Antonín Lyčka and Milan Nádvorník
    A study of reaction of aromatic polynitro compounds with tributylstannyl hydride
    1985, Vol. 50, Issue 11, pp. 2598–2606 [Abstract]
  • Jaromír Kaválek, Josef Jirman and Vojeslav Štěrba
    Kinetics and mechanism of rearrangement and methanolysis of acylphenylthioureas
    1985, Vol. 50, Issue 3, pp. 766–778 [Abstract]
  • Vladimír Macháček, Josef Kořínek, Daniela Kreuzigová and Vojeslav Štěrba
    Kinetics of reactions of 1,2,4-triazole-3-diazonium ions with phenol and with hydroxyl ion
    1985, Vol. 50, Issue 3, pp. 658–674 [Abstract]
  • Jaromír Kaválek, Said El Bahaie and Vojeslav Štěrba
    Kinetics and mechanism of methanolysis of benzoyl derivatives of substituted phenylureas and phenylthioureas
    1984, Vol. 49, Issue 9, pp. 2103–2110 [Abstract]
  • Jaromír Mindl, Vojeslav Štěrba, Vladimír Kadeřábek, Jr. and Jiří Klicnar
    Kinetics and mechanism of hydrolysis of benzhydryl N-arylthiocarbamates and study of their IR spectra
    1984, Vol. 49, Issue 7, pp. 1577–1591 [Abstract]
  • Vladimír Macháček and Antonín Lyčka
    13C and 15N NMR spectra of 6-substituted bicyclo[3,3,1]7-nonanone nitronates
    1984, Vol. 49, Issue 1, pp. 244–252 [Abstract]
  • Antonín Lyčka and Jaromír Kaválek
    13C, 15N, and 19F NMR spectra of 4-fluoro-(3´ or 4´-substituted) azobenzenes
    1984, Vol. 49, Issue 1, pp. 58–64 [Abstract]
  • Jaromír Kaválek, Vladimír Macháček and Vojeslav Štěrba
    Reactions of ethyl 2-alkyl-3-oxobutanoate with thiourea and methylthiourea
    1983, Vol. 48, Issue 7, pp. 1872–1877 [Abstract]
  • Vladimír Macháček, Jaroslav Andrle and Vojeslav Štěrba
    Kinetics of reaction of 1-chloro-2,4,6-trinitrobenzene with enolate ions of 2,4-pentanedione and methyl 3-oxobutanoate
    1983, Vol. 48, Issue 6, pp. 1608–1617 [Abstract]
  • Jaromír Kaválek, Vojeslav Štěrba and Said El Bahaie
    Dissociation constants of m- and p-substituted phenylthioureas and ureas in water and in methanol
    1983, Vol. 48, Issue 5, pp. 1430–1434 [Abstract]
  • Jaromír Mindl and Vojeslav Štěrba
    Kinetics and mechanism of hydrolysis of aryl N-methoxycarbamates and their derivatives
    1983, Vol. 48, Issue 3, pp. 900–905 [Abstract]
  • Jaromír Kaválek, Tomáš Potěšil and Vojeslav Štěrba
    Cyclization kinetics and mechanism of N-benzoyl-N'-(1,2-dimethyl-3-oxo-1-butenyl)thiourea
    1983, Vol. 48, Issue 2, pp. 578–585 [Abstract]
  • Jaromír Kaválek, Jaroslav Novák and Vojeslav Štěrba
    Kinetics of hydrolysis and rearrangements of S-acylthiouronium salts
    1982, Vol. 47, Issue 10, pp. 2702–2710 [Abstract]
  • Jaromír Kaválek, Jiří Hruška and Vojeslav Štěrba
    Kinetics of cyclization of 1-phenyl-3-(1,2-dimethyl-3-oxo-1-butenyl)urea and ethyl 2-methyl-3-N-(N'-phenylureido)-2-butenoate
    1982, Vol. 47, Issue 2, pp. 518–522 [Abstract]
  • Jaromír Kaválek, Pavel Fiedler, Zlata Papoušková and Otto Exner
    The confirmation of trisubstituted ureas and thioureas in solution
    1982, Vol. 47, Issue 1, pp. 35–44 [Abstract]
  • Vladimír Macháček, Vojeslav Štěrba and Helena Zahradníčková
    Solvolysis kinetics and mechanism of 3-methyl-1,3-thiazolidine-2,4-dione
    1981, Vol. 46, Issue 12, pp. 3097–3103 [Abstract]
  • Jaromír Toman, Vojeslav Štěrba and Jiří Klicnar
    Ketimine-enamine tautomerism of 2-ethoxycarbonylmethylene-4-methyl-3-oxo-1,2,3,4-tetrahydroquinoxaline: A kinetic study
    1981, Vol. 46, Issue 9, pp. 2104–2109 [Abstract]
  • Vladimír Macháček, Said El Bahaie and Vojeslav Štěrba
    Study of cyclization of 2-acetyl-3-methylamino-N-benzoyl-2-butenethioamide
    1981, Vol. 46, Issue 1, pp. 256–261 [Abstract]
  • Jaromír Kaválek, Milan Kotyk, Said El Bahaie and Vojeslav Štěrba
    Reactions of N-benzoyl isothiocyanate with anthranilic acid and methyl anthranilate
    1981, Vol. 46, Issue 1, pp. 246–255 [Abstract]
  • Jaromír Kaválek, Said El-Bahaie, Vladimír Macháček and Vojeslav Štěrba
    Study of reaction of thiourea with ethyl 3-oxobutanoate
    1980, Vol. 45, Issue 3, pp. 732–739 [Abstract]
  • Jaromír Kaválek, Said El-Bahaie and Vojeslav Štěrba
    Reactions of thiourea with chloro- and bromoacetic acids
    1980, Vol. 45, Issue 1, pp. 263–268 [Abstract]
  • Jaromír Kaválek, Karel Janák and Vojeslav Štěrba
    Kinetics of reaction of 5-phenyl-1,3,4-thiadiazol-2-diazonium ion with water
    1979, Vol. 44, Issue 10, pp. 3102–3110 [Abstract]
  • Vladimír Macháček, Sylvie Marečková and Vojeslav Štěrba
    Study of reaction of substituted nitrophenyl acetates and benzoates with nucleophiles
    1979, Vol. 44, Issue 6, pp. 1779–1789 [Abstract]
  • Jaromír Kaválek, Ahmad Ashfaq and Vojeslav Štěrba
    Reactions of 1-substituted 2,4,6-trinitrobenzenes with nucleophiles
    1979, Vol. 44, Issue 5, pp. 1453–1459 [Abstract]
  • Vladimír Macháček, Said A. El-bahai and Vojeslav Štěrba
    Kinetics of cyclization of S-ethoxycarbonylmethylisothiouronium chloride to 2-imino-4-thiazolidone
    1979, Vol. 44, Issue 3, pp. 912–917 [Abstract]
  • Jaromír Kaválek, Said El-Bahei and Vojeslav Štěrba
    Hydrolysis kinetics of 4-amino-3-pentene-2-one and its N-substituted derivatives
    1978, Vol. 43, Issue 10, pp. 2732–2739 [Abstract]
  • Jaromír Toman, Jiří Klicnar and Vladimír Macháček
    Synthesis of 2-methyl-3-oxo-3,4-dihydroquinoxaline derivatives
    1978, Vol. 43, Issue 8, pp. 2179–2189 [Abstract]
  • Vladimír Macháček, Jaromír Toman and Jiří Klicnar
    Ketimine-enamine tautomerism of 2-methylene-3-oxo-1,2,3,4-tetrahydroquinoxaline derivatives
    1978, Vol. 43, Issue 6, pp. 1634–1638 [Abstract]
  • Jaromír Kaválek, Miroslav Pastrnek and Vojeslav Štěrba
    Reactions of 2,4,6-trinitrochlorobenzene with dimethyl malonate anion in methanol and methanol-dimethyl sulphoxide mixture
    1978, Vol. 43, Issue 5, pp. 1401–1409 [Abstract]