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Reduction studies on benzaza[3.3.3]propellanc derivatives
Author(s) -
Campaigne E.,
Mehra R. K.
Publication year - 1978
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.5570150138
Subject(s) - chemistry , raney nickel , ketone , sodium borohydride , aluminum hydride , lithium aluminium hydride , medicinal chemistry , lithium (medication) , propellane , flue gas desulfurization , yield (engineering) , bicyclic molecule , organic chemistry , borohydride , catalysis , medicine , materials science , metallurgy , endocrinology , methoxide
Sodium borohydride reduction of 3‐methyl‐2,3‐dioxo‐7,8‐benzo‐3‐aza[3.3.3]propellan‐6‐one (1b) gave 2,4‐dioxo‐3‐methyl‐7,8‐benzo‐3‐aza[3.3.3]propellan‐6‐ol, while lithium aluminum hydride reduction gave 3‐methyl‐7,8‐benzo‐3‐aza[3.3.3]propellan‐6‐ol, which on oxidation, gave the corresponding ketone. This ketone formed the corresponding thioketal upon reaction with 1,2‐ethanedithiol. Raney nickel desulfurization of the thioketal provided 3‐methyl‐6,7‐benzo‐3‐aza[3.3.3]propellane. The same compound was also obtained in poor yield by forming the thioketal of Ib followed by lithium aluminum hydride reduction and Raney nickel desulfurization of the product. Desulfurization of the thioketal of Ib gave 2,4‐dioxo‐6,7‐Benzo‐3‐aza[3.3.3]propellane.