Study of conditions for streamlined assembly of a model bacteriochlorophyll from two dihydrodipyrrin halves

2021 ◽  
Author(s):  
Khiem Chau Nguyen ◽  
Pengzhi Wang ◽  
Jonathan S. Lindsey
Keyword(s):  
Knoevenagel Condensation ◽  
Ring Closure ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Nazarov Cyclization ◽  
Double Ring

Knoevenagel condensation followed by double-ring closure (Nazarov cyclization, electrophilic aromatic substitution, elimination of methanol) and optional zinc insertion smoothly afford models of the native bacteriochlorophylls.

Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization – electrophilic aromatic substitution

2004 ◽  
Vol 82 (2) ◽  
pp. 375-385 ◽  
Author(s):  
Cindy C Browder ◽  
Fredrik P Marmsäter ◽  
F G West
Keyword(s):  
Low Temperature ◽  
Lewis Acid ◽  
Quantitative Yield ◽  
Electrophilic Aromatic Substitution ◽  
Side Chains ◽  
Aromatic Substitution ◽  
Nazarov Cyclization ◽  
Efficient Construction

1,4-Dien-3-ones substituted with pendant arylethyl side chains attached at C-1 were readily prepared from substituted dihydrocinnamaldehydes. Treatment with TiCl4 at low temperature effected domino Nazarov electrocyclization – arene trapping within 5 min to give racemic benzohydrindenones in near-quantitative yield and with complete diastereoselectivity.Key words: domino process, electrophilic aromatic substitution, Lewis acid, Nazarov cyclization.

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