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Benzomorphan related compounds. XIII. Syntheses of 2,6‐methanopyrrolo[1,2‐ d ] [1,4]diazocines
Author(s) -
Bosch J.,
Mauleón D.,
Granados R.
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170541
Subject(s) - chemistry , aluminum hydride , borohydride , amine gas treating , lithium (medication) , pyridine , lithium aluminium hydride , cyclic amines , hydride , medicinal chemistry , sodium borohydride , stereochemistry , organic chemistry , hydrogen , catalysis , medicine , methoxide , endocrinology
Two alternative syntheses of 2,6‐methanopyrrolo[1,2‐ d ][1,4]diazocines (I) based in the acidic cyclization of 2‐(1‐pyrrolylmethyl)tetrahydropyridines are described. In the first synthetic route, lithium aluminum hydride reduction of 2‐cyano‐1,4‐dimethyl‐1,2,3,6‐tetrahydropyridine (IIa) followed by reaction of the resulting primary amine with 2,5‐diethoxytetrahydrofuran affords the requisite tetrahydropyridine IVa. An analogous sequence from 2‐cyano‐4,6‐di‐methylpyridine (V) leads to the corresponding 2‐(1‐pyrrolylmethyl)pyridine VII which by quaternization and borohydride reduction yields a mixture of isomeric tetrahydropyridines, precursors of the pyrrolodiazocine systems Ib and Ic. Structural and stereochemical assignment of the synthesized compounds are discussed.