90779-10-5Relevant academic research and scientific papers
Synthesis of 4H-Thienoazonine and Thienoazecine Derivatives
Browne, Elaine J.
, p. 367 - 379 (2007/10/02)
Derivatives of two new thieno medium-ring heterocyclic systems have been prepared by ring degradation using cyanogen bromide-induced solvolysis of tricyclic bases.Reaction of a hexahydrothienoindolizine (4a) and a hexahydro-7H-thienoquinolizine (4b) with cyanogen bromide and magnesium oxide under solvolytic conditions yielded derivatives of hexahydro-4H-thienoazonine (5a) (6a) and octahydrothienoazecine (5b) (6b), respectively.Functional group interconversions of these medium-ring systems are described, including oxidations to cyclic ketones.The 9a-phenyl derivative of (4a) reacted similarly.By contrast 10b-phenylderivatives (10a,b) of a hexahydropyrroloisoquinoline reacted under these conditions to give medium-ring elimination products, derivatives of tetrahydro-1H-3-benzazonines.
