| US 7,470,785 B2 | ||
| Refined routes to chlorin building blocks | ||
| Jonathan S. Lindsey, Raleigh, N.C. (US); Masahiko Taniguchi, Raleigh, N.C. (US); Doyoung Ra, Taejon (Korea, Republic of); Guoning Mo, Ontario (Canada); and Thiagarajan Balasubramanian, Raleigh, N.C. (US) | ||
| Assigned to North Carolina State University, Raleigh, N.C. (US) | ||
| Filed on Mar. 04, 2005, as Appl. No. 11/72,196. | ||
| Application 11/072196 is a division of application No. 10/140654, filed on May 08, 2002, granted, now 6,946,552. | ||
| Claims priority of provisional application 60/289985, filed on May 10, 2001. | ||
| Prior Publication US 2005/0165228 A1, Jul. 28, 2005 | ||
| Int. Cl. C07B 47/00 (2006.01) | ||
| U.S. Cl. 540—145 | 6 Claims |
1. A method of making a tetrahydrobilene of Formula XI:
 K1, K2 and K4 are hetero atoms independently selected from the group consisting of NH , O, S, Se, Te, and CH2;
K3 is N;
S1, S2, S3, S4, S5, S6, S7, S8, S9, S10, S11, S12, S13, and S14 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 S1, S2, S3, S4, S5, S6, S7, S8, S9, S10, S11, S12, S13, and S14 may optionally be independently selected linking groups Q, wherein said linking groups Q are of the formula:
R1—R2nR3—Y
wherein;
n is from 0 to 10;
R3 may be present or absent;
R1, R2, and R3 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
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