52426-94-5Relevant articles and documents
A new synthesis of push-pull pyrroles, their oxidation to stable 3H-pyrroles and an unexpected anellation reaction
Buehrdel, Gunther,Beckert, Rainer,Herzigova, Petra,Petrlikova, Eva,Schuch, Dirk,Birckner, Eckhard,Goerls, Helmar
experimental part, p. 3404 - 3412 (2011/02/28)
A. new synthesis of push-pull pyrroles of type 5 was developed starting from. bis(imidoyl chlorides) 1 and various iminodiacetic acid derivatives 3. The use of appropriate N-trifluoroacetyl residues as protecting/activating group proved to be the method, of choice for the straightforward, preparation of the 3,4-diarylamino-lH-pyrroles 5. When benzothiazole substructures are present in 2,5-position of heterocycles 5, a two-electron oxidation leads to 3H-pyrroles of type 6 in excellent yields. However, in the case of cyano or ester groups, a further oxidative process immediately led to the new 3H-pyrrolo[3,4-b] quinoxalines 7 via intramolecular ring anellation. 2009 Wiley-VCH Verlag GmbH & Co. KGaA,.
A new synthesis of bis-enaminones via acylation of ketones
Buehrdel, Gunther,Beckert, Rainer,Petrlikova, Eva,Herzigova, Petra,Klimesova, Vera,Fleischhauer, Jan,Goerls, Helmar
experimental part, p. 3071 - 3080 (2009/04/06)
A short and efficient synthesis for a series of 1,6-diaryl-3,4- diarylaminohexa-2,4-diene-1,6-diones was developed. Based on the acylation-prototropism sequence during the reaction of various aryl methyl ketones with bis-imidoyl chlorides, the products were isolated in good yields. Substituted acetophenones, acetylthiophene, 3-acetylpyridine, and acetylferrocene can be integrated into this reaction as ketone component. Similarly, α-tetralone can be transformed with bis-electrophiles into the corresponding bis-enaminones. Treatment of 2-acetylpyridine with N,N′-bis(4-tolyl)ethanebis(imidoyl) dichloride yielded not only the expected bis-enaminone, but also a new quinolizine derivative which was structurally characterized by single crystal X-ray analysis. Analogously, pinacolone and cyclopropyl methyl ketone can readily be converted into bis-enaminones. Monoimidoyl chlorides showed the same reactivity, providing derivatives in high yields. Georg Thieme Verlag Stuttgart.