Reactivity of 3-Ethoxycarbonyl Isoquinolinium Salts Towards Various Nucleophilic Reagents Applications to the Synthesis of New 1,2-Dihydroisoquinoline-3-carboxylates 英文参考文献.docVIP

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Reactivity of 3-Ethoxycarbonyl Isoquinolinium Salts Towards Various Nucleophilic Reagents Applications to the Synthesis of New 1,2-Dihydroisoquinoline-3-carboxylates 英文参考文献.doc

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Reactivity of 3-Ethoxycarbonyl Isoquinolinium Salts Towards Various Nucleophilic Reagents Applications to the Synthesis of New 1,2-Dihydroisoquinoline-3-carboxylates 英文参考文献

Molecules, 2002, 7, 252-263 molecules ISSN 1420-3049 Reactivity of 3-Ethoxycarbonyl Isoquinolinium Salts Towards Various Nucleophilic Reagents: Applications to the Synthesis of New 1,2-Dihydroisoquinoline-3-carboxylates. Mohamed Ameziane A?t Amer Meziane and Jean Pierre Bazureau* Université de Rennes 1, Institut de Chimie, Synthèse Electrosynthèses Organiques 3 (SESO 3), UMR-CNRS 6510, Bat. 10A, Campus de Beaulieu, Avenue du Général Leclerc, CS 74205, 35042 RENNES Cedex, France. Phone : +(33) 02 23 23 66 03, Fax : +(33) 02 23 23 63 74. * Author to whom correspondence should be addressed; E-mail: jean-pierre.bazureau@univ-rennes1.fr Received: 16 January 2002; in revised form: 19 February 2002 / Accepted 20 February 2002/ Published: 28 February 2002 Abstract: Different types of novel 1,2-disubstituted 1,2-dihydro isoquinolines were synthesized by addition reactions of organolithium, alcoholates and borohydride reagents with various isoquinolinium salts. The leaving group character of the isoquinoline moiety was also evidenced. Keywords: 1,2-dihydro isoquinoline, lipophilic isoquinolinium, solvent-free quaternization, organolithium, alcoholate, N,O-acetal, domino reaction. Introduction In a recent paper [1] we have reported that the reaction of lipophilic 3-ethoxy-carbonyl-N-alkyl- isoquinolinium perfluorobutanesulfonate with Grignard reagents provides a very pratical entry to stable 1,2-disubstituted 1,2-dihydroisoquinoline-3-carboxylates (DIC) [2]. The 1,2-dihydroiso- quinoline-3-carboxylic acid derivatives are usually considered to be very air-sensitive species and are rather difficult to purify [3]. In an attempt to overcome the limitations of the standard methods [4], we have now found that the presence of an electron-attracting carboxyl function adjacent to the imino bond increases the stability of N-alkyl isoquinolinium salts. Therefore, the 1,2-addition of vari