A One‐Pot Synthesis of 1,2‐Dihydroisoquinoline Derivatives from Isoquinoline via a Four‐Component Reaction |
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| Authors: | Abdolali Alizadeh Nasrin Zohreh |
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| Institution: | 1. Department of Chemistry, Tarbiat Modares University, P.?O. Box 14115‐175, Tehran, Iran, (phone: +98‐21‐88006631;2. fax: +98‐21‐88006544) |
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| Abstract: | A four‐component reaction for the synthesis of 1,2‐dihydroisoquinoline derivatives is described. The Huisgen 1,4‐dipolar intermediate, which is produced from isoquinoline and an electron‐deficient acetylene compound 1 , reacts with H2O in the presence of diketene to produce 1,2‐dihydroisoquinoline derivatives 2 (Scheme 1). In addition, reaction of isoquinoline, dibenzoylacetylene (=1,4‐diphenylbut‐2‐yne‐1,4‐dione), and diketene in the presence of H2O leads to pyrroloisoquinoline derivative 7 . The structures of the compounds 2a – f and 7 were corroborated spectroscopically (IR, 1H‐ and 13C‐NMR, EI‐MS) and by elemental analyses. A plausible mechanism for the reaction is proposed (Schemes 2 and 3). |
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| Keywords: | Acetylene compounds electron‐deficient Isoquinoline Diketene But‐2‐yne‐1 4‐dione 1 4‐diphenyl‐ Multicomponent reaction Huisgen 1 4‐dipolar intermediate |
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