N-substituted Lactams Research Articles

Sulfidierung ausgewählter Carbonsäure- und Kohlensäureamide mit dem (9-BBN)2S-Reagenz

Sulfidation of Selected Carboxylic and Carbonic Acid Amides with the (9-BBN)2S-Reagent The sulfidation of eight carboxylic and carbonic acid amides (A–H) with bis(1,5-cyclooctanediylboryl) sulfide (1) is described. From the aliphatic acyclic amide A and the N-substituted lactams C–E the corresponding thiocarbonyl compounds 2a and 2c–e, resp., are obtained in high yields. N,N-Dimethylbenzamide (B) reacts with 1 to give monothiobenzoic acid 9-BBN ester (3) and further dithiobenzoic acid 9-BBN ester (4). From N-methylphthalimide (F) and 1 the dithio derivative 5f is formed at room temperature. The carbonic acid amides (urea derivative G, caffeine H) are sulfidated slower than the carboxylic acid amides with formation of the monothio derivatives 2g and 2h, resp. H reacts regioselectively with 1 to yield 6-thiocaffeine (2h) and further to give 2,6-dithiocaffeine (5h).

ChemInform Abstract: Efficient Synthesis of N‐Substituted Lactams from (N‐Arylsulfonyloxy)amines and Cyclic Ketones.

Abstract A new method is reported for the direct preparation of N-substituted lactams from cycloalkanones. N-(p-nitrobenzenesulfonoxyl) methylamine 1a (CH3NH-OSO2C6H4NO2) was reacted with a series of cycloalkanones to give good yields of N-methyl lactams. An addition-rearrangement pathway accounts for the ring-expanded lactam products. A series of N-alkyl-N-arylsulfonoxyl amines were generated in situ and reacted with cyclobutanone to give N-alkyl pyrrolidinones in high yields.

Efficient synthesis of N-substituted lactams from (N-arylsulfonyloxy) amines and cyclic ketones

Abstract A new method is reported for the direct preparation of N-substituted lactams from cycloalkanones. N-(p-nitrobenzenesulfonoxyl) methylamine 1a (CH3NH-OSO2C6H4NO2) was reacted with a series of cycloalkanones to give good yields of N-methyl lactams. An addition-rearrangement pathway accounts for the ring-expanded lactam products. A series of N-alkyl-N-arylsulfonoxyl amines were generated in situ and reacted with cyclobutanone to give N-alkyl pyrrolidinones in high yields.

Polymerization of N‐substituted lactams

AbstractThis study deals with a comparison of the rates and activation parameters of the polymerizations of N‐methyl and N‐benzoyl derivatives of lactams containing 4, 9 or 13 ring atoms initiated by carboxylic acids, amino acids, strong protonic acids or Lewis acids. The respective polymerization mechanisms of substituted and unsubstituted lactams are discussed. The initiators mentioned above lead to the polymerization mechanisms with activated monomer in most cases. The use of stable carbenium cations results in a new type of polymerization of N‐benzoyl lactams with a cationic propagation centre on the chain.

ChemInform Abstract: INDUCTION OF DIFFERENTIATION OF LEUKEMIA CELLS IN VITRO BY N‐SUBSTITUTED AMIDES, LACTAMS, AND 2‐PYRIDONES

Chemischer InformationsdienstVolume 13, Issue 5 Heterocyclic Compounds ChemInform Abstract: INDUCTION OF DIFFERENTIATION OF LEUKEMIA CELLS IN VITRO BY N-SUBSTITUTED AMIDES, LACTAMS, AND 2-PYRIDONES C. LI, C. LISearch for more papers by this authorE. L. SCHWARTZ, E. L. SCHWARTZSearch for more papers by this authorS. L. MELLA, S. L. MELLASearch for more papers by this authorL. S. RITTMANN, L. S. RITTMANNSearch for more papers by this authorA. C. SARTORELLI, A. C. SARTORELLISearch for more papers by this author C. LI, C. LISearch for more papers by this authorE. L. SCHWARTZ, E. L. SCHWARTZSearch for more papers by this authorS. L. MELLA, S. L. MELLASearch for more papers by this authorL. S. RITTMANN, L. S. RITTMANNSearch for more papers by this authorA. C. SARTORELLI, A. C. SARTORELLISearch for more papers by this author First published: February 2, 1982 https://doi.org/10.1002/chin.198205231Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume13, Issue5February 2, 1982 RelatedInformation

Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.

N-Substituted amides, lactams, and 2-pyridones were examined for their ability to induce leukemic cell differentiation in vitro. These substituted amides were effective inducers of the differentiation of murine erythroleukemia (Friend) cells, as judged by the cellular accumulation of hemoglobin. N-Substitution increases the effectiveness of all classes of agents as inducers of maturation as judged by an increase in potency. N-Cyclohexylacetamide appeared to be a particularly effective compound, causing 92% of the population to synthesize hemoglobin at a concentration which was not inhibitory to cell replication. In the lactam series, an increase in ring size was paralleled by an increase in the potency of unsubstituted compounds, but ring size had less effect on N-substituted lactams. Increasing the chain length of the N-alkyl substituent had little additional effect on a series of lactam and 2-pyridone derivatives; however, some decrease in maximal induction occurred with butyl- and hexyl-substituted 2-pyridones. N-Isopropyl-2-pyridone, selected for further study, was as good an inducer of the HL60 human promyelocytic leukemia as it was of the Friend murine erythroleukemia.

Lactams. XIII Alkylation of lactim ethers: A novel synthetic route to N-(2-arylethyl)lactams from N-unsubstituted lactams.

Treatment of the lactim ethers (10a-d, 11a-c), prepared from N-unsubstituted 5-, 6-, and 7-membered lactams (6a-d), with phenacyl bromide or 3, 4-dimethoxyphenacyl bromide in N, N-dimethylformamide at 60°for 1-6 hr furnished the corresponding N-substituted lactams (21a-d, 22a-c) in good yields. Conversion of the lactam ketones (21a-d, 22a-c) into the N-(2-arylethyl) lactams (25a-d, 26a-c) through the lactam alcohols (23a-d, 24a-c) was effected in excellent overall yields by NaBH4 reduction followed by catalytic hydrogenolysis. In contrast, the alkylations of O-methylvalerolactim (10b) or O-ethylvalerolactim (11b) with less reactive alkyl halides (relative to phenacyl bromide) such as MeI, EtI, PhCH2Br, PhCH2CH2Br, and 3, 4-(MeO)2C6H3CH2CH2Br were found to give mixtures of the normally N-alkylated 2-piperidones and N-methyl-or N-ethyl-2-piperidone presumed to have formed by the O→N methyl or ethyl migration during the reactions. Alkylations of the δ-valerolactam anion with 2-arylethyl bromide or its equivalents could afford the corresponding N-substituted 2-piperidones, but in unacceptable yields.

ChemInform Abstract: POLYMERIZATION OF N‐SUBSTITUTED LACTAMS. PART V. ANIONIC POLYMERIZATION OF 2‐PYRROLIDONE

Chemischer InformationsdienstVolume 7, Issue 16 Preparative Organic Chemistry ChemInform Abstract: POLYMERIZATION OF N-SUBSTITUTED LACTAMS. PART V. ANIONIC POLYMERIZATION OF 2-PYRROLIDONE J. BUDIN, J. BUDINSearch for more papers by this authorJ. KRALICEK, J. KRALICEKSearch for more papers by this author J. BUDIN, J. BUDINSearch for more papers by this authorJ. KRALICEK, J. KRALICEKSearch for more papers by this author First published: April 20, 1976 https://doi.org/10.1002/chin.197616092AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume7, Issue16April 20, 1976 RelatedInformation

ChemInform Abstract: POLYMERIZATION OF N‐SUBSTITUTED LACTAMS PART 3, THE KINETICS AND MECHANISM OF POLYMERIZATION OF N‐METHYL‐, N‐BUTYL‐ AND BENZYLCAPRYLLACTAM INITIATED WITH HYDROGEN CHLORIDE

Chemischer InformationsdienstVolume 6, Issue 14 Preparative Organic Chemistry ChemInform Abstract: POLYMERIZATION OF N-SUBSTITUTED LACTAMS PART 3, THE KINETICS AND MECHANISM OF POLYMERIZATION OF N-METHYL-, N-BUTYL- AND BENZYLCAPRYLLACTAM INITIATED WITH HYDROGEN CHLORIDE B. MASAR, B. MASARSearch for more papers by this authorJ. SEBENDA, J. SEBENDASearch for more papers by this author B. MASAR, B. MASARSearch for more papers by this authorJ. SEBENDA, J. SEBENDASearch for more papers by this author First published: April 8, 1975 https://doi.org/10.1002/chin.197514095AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume6, Issue14April 8, 1975 RelatedInformation

ChemInform Abstract: POLYMERIZATION OF N‐SUBSTITUTED LACTAMS PART 2, ACIDOLYTIC CLEAVAGE IN THE POLYMERIZATION OF N‐METHYLCAPRYLLACTAM INITIATED WITH ANHYDROUS HYDROGEN CHLORIDE

Chemischer InformationsdienstVolume 5, Issue 49 Preparative Organic Chemistry ChemInform Abstract: POLYMERIZATION OF N-SUBSTITUTED LACTAMS PART 2, ACIDOLYTIC CLEAVAGE IN THE POLYMERIZATION OF N-METHYLCAPRYLLACTAM INITIATED WITH ANHYDROUS HYDROGEN CHLORIDE B. MASAR, B. MASARSearch for more papers by this authorJ. SEBENDA, J. SEBENDASearch for more papers by this author B. MASAR, B. MASARSearch for more papers by this authorJ. SEBENDA, J. SEBENDASearch for more papers by this author First published: December 10, 1974 https://doi.org/10.1002/chin.197449122AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume5, Issue49December 10, 1974 RelatedInformation

Electrolytic Benzoyloxylation of N, N-Disubstituted Formamides, N-Substituted Lactams, and N-Substituted Cyclic lmides

The electrolytic benzoxylation of N, N-disubstituted formamides, N-methyllactams, and cyclic N-methyl imides with benzoic acid has been studiedi with N, N-disubstituted formamides, the current efficiency for the formation of ester-amides decreased as bulkiness of the substituent increased. The steric effect of N-alkyl groups was conspicuous. ln the case of N-methylformanilide, electrolytic benzoxylation did not occur, and this fact might be due probably to the presence of ev-phenyl group to nitrogen atom. Electrolysis of formamides of eyclic amine and N-methyllactams at low current density gave ester-amides in high current effciency. In the electrolytic benzoxylatien of N-methylsuccinimide the correponding ester-amide was produced in very low yield, and the reaction did not occur at all in the case of N-methylphthalimide. Ester-amides had a benzoylexy group substituted at α -position to nitrogen atom. ln the case of N-methyllactams and cyclic N-methyl imides substitution occurred at N-methyl group. This fact shows that the benzoyloxy group does not attack the methylene group in a ring.

Determination of the basicity of certain N-substituted lactams by the method of IR spectroscopy

1. The shifts of the valence vibrations ΔνOD and ΔνOH and the constants of association with, phenol were found for 11 lactams. 2. The nature of the dependence of the basicity of lactams on the size of the ring was confirmed. The dependence of the basicity on the nature of the substituent was found. 3. The association of phenol with lactams at the carbonyl group does not exclude the possibility of association at the nitrogen.

Synthesis of s-substituted derivatives of cyclic thionamides

A new preparative method for synthesizing S-substituted derivatives of cyclic thionamides by the cleavage of salts of thionamides with five-, six-, and seven-membered rings has been developed. It has been shown that the onium salts of the N-substituted derivatives of cyclic thionamides undergo cleavage at the C-S bond under the action of water or a weak base with the formation of N-substituted lactams and mercaptans.

Polymerization of N-substituted lactams : R. S. Muromova, A. A. Strepikheev and Z. A. Rogovin, Vysokomol. soyed. 5: No. 7, 1096–1100, 1963

Polymerization of N-substituted lactams : R. S. Muromova, A. A. Strepikheev and Z. A. Rogovin, Vysokomol. soyed. 5: No. 7, 1096–1100, 1963