Silylated derivatives of aromatic heterocycles

A compound of Formula (I), (II), (III), or (IV):

• wherein
• m is 0, 1, or 2;
• R1 is independently optionally substituted C1-12 alkyl, optionally substituted C1-12 heteroalkyl, an optionally substituted aryl, or optionally substituted heteroaryl, and, if substituted, the substituents are independently alkyl, alkenyl, aryl, heteroaryl, hydroxyl, C1-C20 alkoxy, C5-C20 aryloxy, C2-C20 alkoxycarbonyl, C5-C20 aryloxycarbonyl, optionally protected amino, optionally protected carboxyl, carboxylato, cyano, halo, phosphonato, phosphoryl, phosphanyl, phosphino, sulfonato, C1-C20 alkylsulfanyl, C5-C20 arylsulfanyl, C1-C20 alkyl sulfonyl, C5-C20 aryl sulfonyl, C1-C20 alkylsulfinyl, C5-C20 arylsulfinyl, sulfonamido, amido, imino, nitro, nitroso, mercapto, optionally protected formyl, C1-C20 thioester, cyanato, thiocyanato, isocyanate, thioisocyanate, carbamoyl, epoxy, styrenyl, silyl, silyloxy, siloxazanyl, boronato, or boryl;
• R2 is H;
• an optionally substituted linear, branched, cyclic, and/or heteroatom-containing alkyl;
• or a halo, protected hydroxy, C1-C24 alkoxy, C2-C24 alkenyloxy, C2-C24 alkynyloxy, C5-C24 aryloxy, C6-C24 aralkyloxy, C6-C24 alkaryloxy, optionally protected C1-C24 alkylcarbonyl (—CO-alkyl), optionally protected C6-C24 arylcarbonyl (—CO-aryl)), C2-C24 alkylcarbonyloxy (—O—CO-alkyl), C6-C24 arylcarbonyloxy (—O—CO-aryl)), C2-C24 alkoxycarbonyl ((CO)—O-alkyl), C6-C24 aryloxycarbonyl (—(CO)—O-aryl), halocarbonyl, C2-C24 alkylcarbonato, C6-C24 arylcarbonato, optionally protected carboxy (—COOH), carboxylato (—COO—), carbamoyl (—(CO)—NH2), mono-(C1-C24 alkyl)-substituted carbamoyl (—(CO)NH(C1-C24 alkyl)), di-(C1-C24 alkyl)-substituted carbamoyl (—(CO)—N(C1-C24 alkyl)2), mono-(C1-C24 haloalkyl)-substituted carbamoyl (—(CO)—NH(C1-C24 alkyl)), di-(C1-C24 haloalkyl)-substituted carbamoyl (—(CO)—N(C1-C24 alkyl)2), mono-(C5-C24 aryl)-substituted carbamoyl (—(CO)—NH-aryl), di-(C5-C24 aryl) substituted carbamoyl (—(CO)—N(C5-C24 aryl)2), di-N—(C1-C24 alkyl), N—(C5-C24 aryl)-substituted carbamoyl, thiocarbamoyl (—(CS)—NH2), mono-(C1-C24 alkyl)-substituted thiocarbamoyl (—(CO)—NH(C1-C24 alkyl)), di-(C1-C24 alkyl)-substituted thiocarbamoyl (—(CO)—N(C1-C24 alkyl)2), mono-(C5-C24 aryl) substituted thiocarbamoyl (—(CO)—NH-aryl), di-(C5-C24 aryl)-substituted thiocarbamoyl (—(CO)—N(C5-C24 aryl)2), di-N—(C1-C24 alkyl), N—(C5-C24 aryl)-substituted thiocarbamoyl, carbamido (—NH—(CO)—NH2), cyano(—C≡N), cyanato (—O—C═N), thiocyanato (—S—C═N), optionally protected formyl (—(CO)—H), optionally protected thioformyl (—(CS)—H), optionally protected amine, C1-C24 alkylamido (—NH—(CO)-alkyl), C6-C24 arylamido (—NH—(CO)-aryl), imino (—CR═NH where R=hydrogen, C1-C24 alkyl, C5-C24 aryl, C6-C24 alkaryl, C6-C24 aralkyl, C2-C20 alkylimino (—CR═N(alkyl), where R=hydrogen, C1-C24 alkyl, C5-C24 aryl, C6-C24 alkaryl, C6-C24 aralkyl), arylimino (—CR═N(aryl), where R=hydrogen, C1-C20 alkyl, C5-C24 aryl, C6-C24 alkaryl, C6-C24 aralkyl), nitro (—NO2), nitroso (—NO), optionally protected sulfo (—SO2OH), sulfonate (SO2O—), C1-C24 alkylsulfanyl, C5-C24 arylsulfanyl, C1-C24 alkylsulfinyl (—(SO)-alkyl), C5-C24 arylsulfinyl (—(SO)-aryl), C1-C24 alkylsulfonyl (—SO2-alkyl), C1-C24 monoalkylaminosulfonyl-SO2—N(H) alkyl), C1-C24 dialkylaminosulfonyl-SO2—N(alkyl)2, C5-C24 aryl sulfonyl (—SO2-aryl), boronato (—B(OR)2 where R is H, alkyl or other hydrocarbyl), phosphono (—P(O)(OH)2), phosphonato (—P(O)(O)2), phosphinato (P(O)(O—)), phospho (—PO2), or phosphine (—PH2);
• X is NW, O, or S;
• R3 is an amine protecting group, an optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkaryl or optionally substituted alk-heteroaryl;
• is a heteroaromatic moiety containing y additional nitrogens in the ring structure, where y=0 or 1 when X is O or S, or y=0, 1, or 2 when X is NR3;
• and
• is an aromatic moiety containing x nitrogen atoms in the ring structure, where x=0, 1, or 2.