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Synthesis of dihydrolysergol analogues

โœ Scribed by Sergio Mantegani; Gabriella Traquandi; Mario Varasi


Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
64 KB
Volume
38
Category
Article
ISSN
0022-152X

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โœฆ Synopsis


Abstract

As a part of a search for novel biological active ergoline derivatives, the indole ring present in the ergoline skeleton (indole[4,3โ€f,g]quinoline) was converted into different heterocyclic ring systems such as quinazoline 2, benzofurane 3 and benzoxazole 4. Due to the paramount importance of chirality to attain biological activity, natural dihydrolysergic acid 1 was chosen as starting material and a synthetic pathway conservative in term of chirality was followed.


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JMS 0300 apparatus. ## 1. 1-Isopropyl-2.3-dimethoxybenzene (4a). To a s o h of 3a (Aldrich; I00 g, 0.66 mol) in acetone (1 1) and Me2S04 (192.5 ml, 2.03 mol), K,CO, (280 g, 2.03 mol) was added, and the mixture was refluxed with stirring under N, for 45 h. After addition of H,O (1 I), heating was c