- Concise synthesis of the isothiourea organocatalysts homobenzotetramisole and derivatives.
Concise synthesis of the isothiourea organocatalysts homobenzotetramisole and derivatives.
The Journal of organic chemistry (2013-05-22)
Beatrice Ranieri, Omar Robles, Daniel Romo
PMID23688163
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.
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