Nouvelle methode de synthese de tetrahydro-2,3,4,5 benzo (b) 1H-azepines substituees en position -2

Adam, Gérard; Andrieux, Jean; Plat, M.

doi:10.1016/0040-4020(82)87018-x

Cited by 10 publications

(1 citation statement)

References 22 publications

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“…[344] 2-Substituted 4,5-dihydro-3H-benzo[b]azepines have been prepared in a similar manner by reaction of hydrogen azide in benzene in the presence of sulfuric acid. [345] A more practical azidation/rearrangement method involves the addition of sodium azide to a tertiary alcohol and methanesulfonic acid in dichloromethane. [346] 5-Aryl-3,4-dihydro-2H-pyrroles 98; General Procedure: [343] CAUTION: Organic azides are highly unstable and may decompose explosively.…”

Section: Scheme 36 Intramolecular [3 + 2] Cycloaddition Of An In Situmentioning

confidence: 99%

Product Class 7: Imines

Padwa¹,

Bellus²

2005

Category 4. Compounds With Two Carbon Heteroatom Bonds

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Compounds with the general structure R 1 R 2 C=NR 3 , referred to as imines, were first obtained by Schiff via condensation of ketones and aldehydes with primary amines. Therefore, the condensation products are also called Schiff bases. In addition, the nominations azomethine, ketimine (derived from ketones), aldimine (derived from aldehydes), and anil (derived from anilines) are in use. It is recommended that the terms imine(s), ketimine(s), or aldimine(s) are used, rather than Schiff base(s) or azomethine(s).Since imines have to be considered as analogues of carbonyl compounds, many of the chemical properties are similar to the latter. Imines are used in new C-C bond formations, and reactions with electrophiles (e.g., aldehydes, alkyl halides), and the C=N moiety can undergo nucleophilic reactions. Generally, imines are very useful compounds in organic synthesis, as they are used in several syntheses of aza-heterocyclic compounds. Most imines are stable in an alkaline medium and therefore can be dried over potassium hydroxide. In diluted acid, however, they are easily hydrolyzed. In many cases intermediary imines cannot be isolated because of their lability. The presence of a C=N bond creates the possibility for E/Z isomerism (syn/anti). It has been recognized that such geomet-

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