title: Concise synthesis of the isothiourea organocatalysts homobenzotetramisole and derivatives.
abstract: A concise approach to the synthesis of homobenzotetramisole and derivatives is described. Our strategy features a one-pot acylation-cyclization of 2-aminobenzothiazole with α,β-unsaturated acid chlorides to afford annulated pyrimidones. Subsequent Grignard addition followed by acid-promoted dehydration and reduction provides good overall yields of the title compounds in three steps and in quantities up to 10 g. The synthesis employs low-cost and readily available starting materials and enables access to both optical antipodes of these increasingly useful nucleophilic catalysts following chiral separation.
authors.affiliation: Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842-3012, United States.
authors.forename: Beatrice
authors.initials: B
authors.lastname: Ranieri
authors.forename: Omar
authors.initials: O
authors.lastname: Robles
authors.forename: Daniel
authors.initials: D
authors.lastname: Romo