ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Pyrylium Compounds. 30. C-Alkylation of 1,3,5-Triaryl-pentene-1,5-dione Enolates: A Simple Approach to 3-Alkylsubstituted 2,4,6-Triarylpyrylium Salts1,3,5-Triaryl-pentene-1,5-dione enolates (10), obtainable in crystalline form from 2,4,6-triarylpyrylium pseudobases (9) and sodium methoxide in benzene/ether, react in dipolar aprotonic solvents (e.g. DMSO, DMF) with various types of alkyl iodides to give C-alkylation products (11) which afford 3-substituted 2,4,6-triarylpyrylium salts (12) on treatment with perchloric acid. This reaction sequence proved to be a convenient synthetic route to pyrylium salts (12) having 3-oriented substituents such as normal or branched alkyl groups CnH2n+1 (e.g.n = 1-5), isotopically modified alkyl groups (e.g. C[2H3], C2[2H5]), allyl type substituents (e.g. CH2=CHCH2, MeCH=CHCH2, CH2, CH2=CMeCH2) or benzyl groups (e. g. PhCH2, 4-Br—C6H4CH2). Bifunctional alkylating agents (e.g. 1,4-diiodobutane, o-xylylenediiodide) resulted in a novel type of bispyrylium salts (14) with 3,3′-linkage. The pyrylium salts obtained were characterized by their 1H-n.m.r. and u.v. spectra as well as, in most cases, by transformation into the corresponding pyridine derivatives (13) and bispyridines (15) respectively.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19853270616
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