Synthesis of Benzothienoazecine and Benzobenzothienoazecine Derivatives
Derivatives of two new diannulated azecine systems have been prepared by ring degradation of precursor bases with cyanogen-bromide-induced solvolysis.Reaction of a tetrahydro-5H-benzothienoquinlizine (5a) and a tetrahydro-7H-benzobenzothienoquinolizine (5b) with cyanogen bromide and magnesium oxide under solvolytic conditions yielded derivatives of a hexahydrobenzothienoazecine (6a) and a hexahydrobenzobenzothienoazecine (6b), respectively.Functional group interconversions of the medium-ring systems were performed,including oxidations to cyclic ketones.The 5H-benzothienoquinolizine and 7H-benzobenzothienoquinolizine bases (5a) and (5b) are the first reported examples of these ring systems.
Browne, Elaine J.
p. 783 - 790
(2007/10/02)
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