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Synthetic studies towards 1,5-benzodiazocines
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
2013 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, no 12, 2647-2654 p.Article in journal (Refereed) Published
Abstract [en]

Anthranilonitrile reacted with phenylmagnesium bromide to yield a dianion, which when heated (similar to 120 degrees C) yielded the condensation product 2-(2-aminophenyl)-2,4-dipheny1-1,2-dihydroquinazoline 8. This heterocycle, when treated with palladium acetate, was converted into 6,12-diphenyldibenzo[b,f][1,5] diazocine 9. Methylmagnesium bromide and anthranilonitrile, under similar conditions directly gave a nitrogen-bridged diazocine, whose structure was determined by X-ray crystallography and also proven to be an analogue of Troger's base. Acid-induced condensation of 2-amino-3-methoxybenzaldehyde gave the trimeric product 45 rather than a dibenzo[b,f][1,5]diazocine.

Place, publisher, year, edition, pages
2013. Vol. 69, no 12, 2647-2654 p.
Keyword [en]
Benzo[b, f][1, 5]diazocine, Iminodibenzodiazocine, Quinazoline, Nitrogen heterocycle, Grignard reagent, Troger's base
National Category
Chemical Sciences
URN: urn:nbn:se:kth:diva-120161DOI: 10.1016/j.tet.2013.01.018ISI: 000315610400020ScopusID: 2-s2.0-84874106108OAI: diva2:613788

QC 20130402

Available from: 2013-04-02 Created: 2013-04-02 Last updated: 2013-04-02Bibliographically approved

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