Synthesis of 3, 5, 12-triazawurtzitanes (3, 5, 12-triazatetracyclo [5.3. 1.12, 6.04, 9] dodecanes)

AT Nielsen, SL Christian, DW Moore…

Index: Nielsen, Arnold T.; Christian, Stephen L.; Moore, Donald W.; Gilardi, Richard D.; George, Clifford F. Journal of Organic Chemistry, 1987 , vol. 52, # 9 p. 1656 - 1662

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Citation Number: 44

Abstract

CIS. CIS-7 cls. cls-8"(i) ROH, HCl, reflux;(ii) H,, Pt, CH3C02H, 25" C, 20-50 psi;(iii) LiA1H4,(C2H5), 0, reflux;(iv)(COCI),,(CH3), S0,-55" C. 81%; n-Pr, 84%). Use of tetrahydrofuran as reaction solvent in the reduction in place of ether leads to 90-95% yields of 7 from 6c (see Experimental Section). The lower yield with the methyl ester is believed to result from polymerization of some of the intermediates, more facile with the methyl than ...