Intramolecular Mannich Research Articles

Synthesis of (±)-nitramine and (±)-isonitramine

The alkaloids (±)-nitramine (1) and (±)-isonitramine (2) have been synthesised, employing an intramolecular Mannich reaction to set up the spirocyclic ring system.

Reaction of γ-carboxyglutamic acid with aldehydes

The DL-γ-carboxyglutamic acid (Gla) reacts quantitatively with formaldehyde to give 4,4-dicarboxyproline and with other aldehydes to give the racemic diastereoisomers of the 5-substituted 4,4-dicarboxyprolines. The pH-dependent reaction rate and the stereochemical behaviour suggest an intramolecular Mannich mechanism.After heating at 100 °C for 30 min, the 4,4-dicarboxyproline and the 5-substituted 4,4-dicarboxyprolines lose a carboxyl group from C4 to give the racemic diastereoisomers of the cyclic analogs of glutamic acid.

ChemInform Abstract: 10‐HYDROXY‐4‐METHYL‐2,3,4,5,6,7‐HEXAHYDRO‐1,6‐METHANO‐1H‐4‐BENZAZONINE DERIVATIVES (HOMOBENZOMORPHANS) AS ANALGESICS

Abstract7‐M.ethoxy‐1‐tetralon (I) liefert mit Li‐acetonitril das Addukt (II), aus dem durch Reduktion die Amine (IIIa) und (IIIb) zugänglich sind.

10-Hydroxy-4-methyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine derivatives (homobenzomorphans) as analgesics.

Six 10-hydroxy-4-methyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine derivatives 17a-f have been synthesized as potential analgesics. The synthesis of these compounds involved conversion of 4-(2-dimethylaminoethyl)-6-methoxy alpha tetralone derivatives 12a-f to their N-methyl analogues and the subsequent intramolecular mannich reaction with formaldehyde to give the 7-keto C-ring homobenzomorphans 14a-f from which 17a-f, respectively, were obtained. Compounds 17a-f are as potent as morphine as analgesics (mice).

Studies on Benzimidazoles and Related Compounds. III. The Intramolecular Mannich Reaction of 2-Alkylaminomethylbenzimidazoles

The intramolecular Mannich reaction of 2-alkylaminomethylbenzimidazole (II) provided 4-alkyl-1, 3, 4, 5-tetrahydro-1, 3, 6-oxadiazepino [3, 4-a] benzimidazole (III) in a good yield. Moreover, the amine (II) can be regenerated by treatment of III with 15% hydrochloric acid and its mechanism is speculated.

Catalytic reactions involving azomethines. XI. Kinetics of condensation of histamine with 3-hydroxypyridine-4-carboxaldehyde. An intramolecular Mannich reaction

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCatalytic reactions involving azomethines. XI. Kinetics of condensation of histamine with 3-hydroxypyridine-4-carboxaldehyde. An intramolecular Mannich reactionThomas C. Bruice and Anthony LombardoCite this: J. Am. Chem. Soc. 1969, 91, 11, 3009–3014Publication Date (Print):May 1, 1969Publication History Published online1 May 2002Published inissue 1 May 1969https://doi.org/10.1021/ja01039a031RIGHTS & PERMISSIONSArticle Views102Altmetric-Citations13LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (607 KB) Get e-Alerts Get e-Alerts