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The base sequence selectivity for reaction at the guanine-N7 position was examined for a series of structurally related triazenes by a modification of a standard DNA sequencing method. The monomethyl and monochloroethyl triazenes alkylate guanines extensively at the N7 position with a general preference for runs of contiguous guanines, similar to, but not as striking as that observed previously for the chloroethylnitrosoureas. In contrast to the nitrosoureas, the triazenes had patterns of base sequence selectivity that differed somewhat from agent to agent, with the monochloro-ethylphenyltriazene having the pattern most different from the others in the series. Thus, the nature of the nonalkylating portion of the molecule can influence the ultimate alkylation preference. The monoethylating analogues alkylated weakly with little sequence preference, and the dimethyl analogues were essentially unreactive in this system.

TANG. Can. J . Chcm. 62, 741 (1984).The synthesis of somc ncw I-aryl-3-alkyl-3-hydroxymcthyltriazcncs is dcscribcd. Thc mcthod of coupling a diazonium salt with an alkylamine/formaldchyde mixture has been cxtcndcd to (a) somc diazonium ions withl~trrtr substituents other than -M groups, (b) those with substituents in thc nrthn position. and (c) to homologous alkylamincs (c.g. cthylamine, propylaminc, ctc.). Hydroxymethyltriazencs can also bc prcparcd by the rcaction of a I-aryl-3-mcthyltriazene with formaldchydc. Scvcral new derivatives of thc hydroxymcthyl function havc bccn prcparcd. Rcaction with acctic anhydridc or bcnzoyl chloride in pyridine affords respcctivcly the acctoxymcthyl-ant1 benzoyloxymcthyl-trinzcncs; thc acctatcs and bcnzoatcs rcact rcadily with methanol to give the novel mcthoxymethyltriazcncs. This is the first rcport of a scrics of dialkyltriazcncs with an ether linkagc in the a position. An ether of this type has also bccn obtaincd directly from thc diazonium tluoroboratc salt by coupling with a mixturc of benzylamine and formaldchydc in cthanolic solution.

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