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1H-4,5,6,7-tetrahydro-1,3-diazepines. Part I: Synthesis, spectral and chemical properties of 1,2-diaryl derivatives

✍ Scribed by Mónica E. Hedrera; Isabel A. Perillo

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
478 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The synthesis of several 1,2‐diaryl‐1__H__‐4,5,6,7‐tetrahydro‐1,3‐diazepines 1 by cyclization of N‐aryl‐__N'‐benzoyltetramethylenediamines 2 is described. Two alternative synthetic routes to obtain precursors 2 are discussed, being that which employes pyrrolidine as starting material the most convenient. Nucleophilic attack of compounds 1 on methyl iodide affords 1,2‐diaryl‐1__H‐4,5,6,7‐tetrahydro‐1,3‐diazepinium iodides 3. ^1^H‐nmr spectra of these compounds are unequivocally assigned by means of NOESY experiments, ^1^H‐nmr spectra of compounds 1 and 3 are analyzed and compared inter se and with those of compounds 1 run in the presence of trifluoroacetic acid‐d. Reduction of compounds 1 with borane leads regiospecifically to N‐aralkyl‐N'‐aryltetramethylenediamines 7.

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1H-4,5,6,7-Tetrahydro-1,3-diazepines. pa
1H-4,5,6,7-Tetrahydro-1,3-diazepines. part II: basicity and hydrolysis of 1, 2-diaryl derivatives
✍ Mónica E. Hedrera; Isabel A. Perillo; Beatriz Fernández 📂 Article 📅 2001 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 83 KB

## Abstract Basicity and alkaline hydrolysis of 1,2‐diaryl‐1__H__‐4,5,6,7‐tetrahydro‐1,3‐diazepines 1 are studied. Results are analyzed on the basis of Hammett and Swain‐Lupton constants, finding good structure‐basicity correlation when both, inductive and mesomeric effects, are considered together

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ChemInform Abstract: 1H-4,5,6,7-Tetrahydro-1,3-diazepines. Part 2. Basicity and Hydrolysis of 1,2-Diaryl Derivatives.
✍ Monica E. Hedrera; Isabel A. Perillo; Beatriz Fernandez 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 27 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v