Preparation of 4‐hydroxy‐3‐substituted, 2 H ‐1‐benzopyran‐2‐ones and 2 H ‐1‐benzothiopyran‐2‐ones from carboxylic esters and methyl salicylates or methyl thiosalicylate | Zendy

Davis Sharon E. | Zendy; Church A. Cameron | Zendy; Tummons Rebecca C. | Zendy; Beam Charles F. | Zendy

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Preparation of 4‐hydroxy‐3‐substituted, 2 H ‐1‐benzopyran‐2‐ones and 2 H ‐1‐benzothiopyran‐2‐ones from carboxylic esters and methyl salicylates or methyl thiosalicylate

Author(s) -

Davis Sharon E.,

Church A. Cameron,

Tummons Rebecca C.,

Beam Charles F.

Publication year - 1997

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570340411

Subject(s) - chemistry , lithium diisopropylamide , carboxylic acid , lithium (medication) , organic chemistry , benzopyran , medicinal chemistry , bicyclic molecule , methyl salicylate , ion , deprotonation , medicine , ecology , biology , endocrinology

C(α)‐Carboxylic acid esters were treated with excess lithium diisopropylamide, condensed with methyl salicylates or methyl thiosalicylate, followed by acid cyclization to either 4‐hydroxy‐3‐substituted, 2 H ‐1‐benzopyran‐2‐ones (coumarins), or 2 H ‐1‐benzothiopyran‐2‐ones (thiocoumarins).

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