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- W2079891931 endingPage "178" @default.
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- W2079891931 abstract "A new and convenient route for the synthesis of several heterotetra- and pentacyclic compounds is presented. Heating the 2-vinyl-N,N-dialkylanilines 3a-h, synthesized from the aldehydes 2a-f,h or the acetophenone 2g and malononitrile or ethyl cyanoacetate, in refluxing 1-butanol yields selectively the tetra- and pentacyclic compounds 4a-h. This cyclization proceeds via a 1,5 hydrogen shift, followed by an addition of the carbanion to the iminium double bond. The benzo[f]thieno[3,2-a]quinolizine 4c and the benzo[f]thieno[2,3-a]quinolizine 4d represent new classes of heterocycles. The first example of formation of a six-membered ring via carboncarbon bond formation, starting from 2-vinyl-substituted enamines, was the conversion of 5a and 5b into the benzo[h]pyrrolo[1,2-a]-quinoline 6a and the naphtho[2,1-c]quinolizine 6b, respectively. Most probably, the cyclization of 5a and 5b proceeds in the same way as does the cyclization of the 2-vinyl N,N-disubstituted aniline derivatives. Heating the tricyano compound 5c in refluxing 1-butanol gave both the benzo[g]pyrrolo[1,2-a]indole 7 and malononitrile. This cyclization proceeds probably via a 1,6 hydrogen shift, followed by a 1,5 electrocyclization, and a subsequent fast elimination of malononitrile." @default.
- W2079891931 created "2016-06-24" @default.
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- W2079891931 date "1989-01-01" @default.
- W2079891931 modified "2023-10-16" @default.
- W2079891931 title "The “tert-amino effect” in heterocyclic chemistry: Synthesis of tetra- and pentacyclic compounds" @default.
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- W2079891931 doi "https://doi.org/10.1002/recl.19891080503" @default.
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