Synthesis of 1-alkyl-3,4-dihydroisoquinoline derivatives and study of their effect on arterial pressure

Polygalova, N. N.; Михайловский, А. Г.; Лиманский, Е. С.; Syropyatov, B. Ya.; Вахрин, М. И.

doi:10.1007/s11094-006-0076-9

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“…The starting materials for the synthesis of compounds 2, 3 are described in [6,13,14], and of substances 5, 6 in [15]. Drotaverine base was isolated from tablets with a suitable expiry date, mp 58-60°C, its purity was checked by TLC.…”

Section: Methodsmentioning

confidence: 99%

Enamines of the 1,2,3,4-tetrahydroiso-quinoline series in the Chichibabin synthesis of pyrrolo[2,1-a]isoquinolines and in reaction with oxalyl chloride

Polygalova

Михайловский

Vikhareva

et al. 2007

Chem Heterocycl Compd

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Pyrrolo[2,1-a]isoquinolines are used widely in organic synthesis, medicine, and other areas [1]. The classical method of design the pyrrolo[2,1-a]isoquinoline system is the interaction of 1-alkylisoquinolines with α-halo ketones (the Chichibabin reaction) [1,2]. It is known [3] that on cyclization with the formation of condensed systems a determining role is played by the radicals in position 3 of the isoquinoline ring. The aim of the present work is an investigation of the potentialities of this reaction in the presence of two methyl groups in position 3 and also of a different structure for the enamine fragment.The reaction of enamines of the 1,2,3,4-tetrahydroisoquinoline series with oxalyl chloride has also been widely investigated [1,4,5]. In the given examples, both bases, in the molecules of which the structure of the enamine is already fixed, and compounds in the imino form, enter into this reaction. The latter is characteristic for derivatives of 1-alkylisoquinoline [6,7], the alkyl residue in the structure of which, unlike carbonyl or just withdrawing groups, does not aid stabilization of the enamine form. Consequently our aim is the study of the conditions of carrying out and the structures of the products of the named reaction in the presence of an alkyl residue at position 1 of the isoquinoline ring.The investigations showed that the reaction of enamines 1a-c with p-bromophenacyl bromide proceeds readily on boiling in alcohol in the presence of Na 2 CO 3 and compounds 2a-c are formed. On using drotaverine (no-spa) base as the initial enamine the reaction product is compound 2d. Enamino amides and enamino esters of the benzo[f]isoquinoline series, analogous in structure to compounds 1a-c, form the corresponding tetracyclic derivatives 3a-c in this reaction. __________________________________________________________________________________________ Perm State Pharmaceutical Academy,

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