Benzimidazo [1,2-b]isoquinolines have been prepared by a formal [4+2] intramolecular cycloaddition of ketenimines with imines.
Synthesis of isoquinolines by cycloaddition of arynes to 1,2,4-triazines
✍ Scribed by António M.d'A.Rocha Gonsalves; Teresa M.V.D. Pinho e Melo; Thomas L. Gilchrist
- Book ID
- 104204996
- Publisher
- Elsevier Science
- Year
- 1992
- Tongue
- French
- Weight
- 509 KB
- Volume
- 48
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Absfmct: Benxyne has been generated from benzencdiezonimn-2carboxylate in the presence of several 1,2,4triaxinea 1 snd isoquinolines 2 have been is&ted ia inodeam yield. I-Aminobenarkole was also used as the scurce of benxyne and kxpinolines went again is&ted in mode&e yield from these react&s CMe&ykuyne, which was generated from 5-methybhranilic acid, reacted unselectively with the trkines to give mixtmes of d and 7-methylisaquinolines 3 and 4 On the ok hand reactions of 3-methylbenzyne with the hiazines Id aid le promded
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Formal [4 + 2] Intramolecular Ketenimine-Imine Cycloaddition. Synthesis of Benzimidazo[1,2-b]isoquinolines. -Formal [4+2] cycloaddition of ketenimine intermediates (V) derived from the azides (III) and diphenylketene (IV) by aza-Wittig reaction, provides the partially saturated compounds (VI). They
Ethyl 1,2,4-triazine-5-carboxylates 6 were prepared by heating N,N-dimethylaminomethyleneor ethoxymethylenehydrazones 5 with ammonium acetate in acetic acid at-100°C. NMR-studies confirmed the absence of their regio isomers (6-carboxylates), showing the high regioselectivity of this procedure. Rece