Journals / Turkish Journal of Chemistry / 2005 / Cilt: 29 - Sayı: 3
Synthesis of Some New Dihalophenyl- and Dihalobenzylisocoumarins and Their (dl)-3,4-Dihydroderivatives
- Journal
- Turkish Journal of Chemistry
- Pages
- 321–325
- DOI
- —
Abstract
3-Dihalophenyl- and dihalobenzylisocoumarins (3a-c) were synthesized by condensation of homophthalic acid (1) with dihalobenzoyl- and dihalophenylacetyl chlorides (2a-c), respectively. The alkaline hydrolysis of these isocoumarins (2a-c) afforded keto-acids (4a-c). (dl)-3-(Dihalophenyl)- and (dl)-3-(dihalobenzyl)- 3,4-dihydroisocoumarins (6a-c) were obtained by reduction of keto-acids (4a-c) to racemic hydroxy-acids (5a-c) followed by cyclodehydration using acetic anhydride.
Özet
3-Dihalophenyl- and dihalobenzylisocoumarins (3a-c) were synthesized by condensation of homophthalic acid (1) with dihalobenzoyl- and dihalophenylacetyl chlorides (2a-c), respectively. The alkaline hydrolysis of these isocoumarins (2a-c) afforded keto-acids (4a-c). (dl)-3-(Dihalophenyl)- and (dl)-3-(dihalobenzyl)- 3,4-dihydroisocoumarins (6a-c) were obtained by reduction of keto-acids (4a-c) to racemic hydroxy-acids (5a-c) followed by cyclodehydration using acetic anhydride.