Patent ID: 7470785

Claim:
A method of making a tetrahydrobilene of Formula XI: wherein: K 1 , K 2 and K 4 are hetero atoms independently selected from the group consisting of NH , O, S, Se, Te, and CH 2 ; K 3 is N; S 1 , S 2 , S 3 , S 4 , S 5 , S 6 , S 7 , S 8 , S 9 , S 10 , S 11 , S 12 , S 13 , and S 14 are independently selected from the group consisting of H, aryl, phenyl, cycloalkyl, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, perfluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl; and wherein from one to four of S 1 , S 2 , S 3 , S 4 , S 5 , S 6 , S 7 , S 8 , S 9 , S 10 , S 11 , S 12 , S 13 , and S 14 may optionally be independently selected linking groups Q, wherein said linking groups Q are of the formula: R 1 —R 2 n R 3 —Y wherein; n is from 0 to 10; R 3 may be present or absent; R 1 , R 2 , and R 3 are each independently selected from the group consisting of ethene, ethyne, aryl, and heteroaryl groups, which aryl and heteroaryl groups may be unsubstituted or substituted one or more times with H, aryl, phenyl, cycloalkyl, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, perfluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl; Y is a protected or unprotected reactive substituent selected from the group consisting of hydroxy, thio, seleno, telluro, ester, carboxylic acid, boronic acid, phenol, silane, sulfonic acid, phosphonic acid, alkylthiol, formyl, halo, alkenyl, alkynyl, haloalkyl, alkyl phosphonate, alkyl sulfonate, alkyl carboxylate, and alkyl boronate groups; and Z is selected from the group consisting of halo, alkoxy, and acyloxy; said method comprising condensing a compound of Formula WH with a compound of Formula EH in an organic solvent in the presence of an acid to form a tetrahydrobilene of Formula XI.