Solid-Phase Traceless Synthesis
1101
1
1
3
H); 8.39 (s, 1 H); 16a: 4.01 (s, 2 H); 6.76 (d, 1 H, J = 8); 7.12 (d, 1 H, J = 8); 7.20 (s, 1 H);
6b: 1.25 (d, 3 H, J = 6); 4.04 (q, 1 H, J1 = 6, J2 = 7); 6.87 (s, 1 H); 7.09 (s, 1 H); 17d : 0.78 (d,
H, J = 7); 0.95 (d, 3 H, J = 7); 1.22 (d, 3 H, J = 7); 1.24 (d, 3 H, J = 7); 3.65 (m , 1 H); 3.88
(
m , 1 H); 7.38 (s, 1 H); 7.60 (s, 1 H); 17e: 2.97 (m , 4 H); 3.74 (m , 4 H); 7.33 (s, 1 H); 7.49 (s,
1
1
7
3
H); 8.15 (s, 1 H); 17f: 5.22 (s, 2 H); 5.71 (s, 1 H); 5.95 (s, 1 H); 7.72 (d, 1 H, J = 8); 7.79 (s,
H, J = 8); 8.06 (d, 1 H); 8.45 (s, 1 H); 17g: 2.21 (s, 3 H); 5.47 (s, 2 H); 7.11 (d, 2 H, J = 8);
.15 (d, 2 H, J = 8); 7.65 (d, 1 H, J = 8); 7.70 (s, 1 H); 8.04 (d, 1 H, J = 8); 8.46 (s, 1 H); 17h :
.85 (s, 3 H); 5.48 (s, 2 H); 6.87 (d, 2 H, J = 9); 7.24 (d, 2 H, J = 9); 7.65 (d, 1 H, J = 8); 7.79
(
s, 1 H); 8.05 (d, 1 H, J = 8); 8.48 (s, 1 H).
Mesylation (Resin 18)
A polypropylen e 5-m l fritted syrin ge was ch arged with 100 m g of resin 10c, th e resin was
wash ed th ree tim es with pyridin e, an d a 1 M solution of m esyl ch loride in pyridin e was
added. Th e syrin ge was left on a tum bler for 2 h . Th e resin was wash ed th ree tim es with
pyridin e, th ree tim es with DMF, th ree tim es with DCM, th ree tim es with MeOH.
Syn th esis of Tetrah ydroquin oxalin es 21
A glass vial was ch arged with 50 m g of dry resin 20 an d 2 m l of TFA was added. Th e resin
was gen tly sh aken for 2 h , th en filtered off an d wash ed twice with TFA. Th e extracts were
pooled an d TFA was evaporated in a stream of n itrogen . Th e structure an d properties of
1
com poun ds 21 are given in Fig. 6 an d Table VIII. H NMR spectra (500 MHz, DMSO-d ) of
6
2
1
1
1a: 3.28 (q, 2 H, J1 = 3, J2 = 11); 3.39 (m , 2 H); 6.52 (d, 1 H, J = 8); 6.75 (s, 1 H); 6.77 (d,
H, J = 8); 21b: 1.12 (d, 3 H, J = 6); 2.84 (q, 1 H, J1 = 8, J2 = 11); 3.30 (q, 1 H, J1 = 3, J2
1); 3.41 (m , 1 H); 6.55 (d, 1 H, J = 8); 6.78 (s, 1 H); 6.80 (d, 1 H, J = 8); 21c: 2.83 (q, 1 H,
=
J1 = 8.5, J2 = 14); 2.89 (q, 1 H, J1 = 8.5, J2 = 19); 3.01 (q, 1 H, J1 = 5, J2 = 13); 3.27 (q, 1 H,
J1 = 2, J2 = 12); 3.88 (m , 1 H); 5.72 (d, 2 H, J = 2); 6.94 (d, 1 H, J = 9); 7.24 (m , 3 H); 7.31 (d,
2
H, J = 6); 7.34 (d, 1 H, J = 9); 7.38 (s, 1 H).
Th iourea Form ation (Resin s 28 an d 34)
A polypropylen e 10-m l fritted syrin ge was ch arged with ≈500 m g of resin 25, an d th e resin
was wash ed th ree tim es with NMP. A 1 M solution (5 m l) of ph en yl isoth iocyan ates in NMP
was added, an d th e reaction was carried out at am bien t tem perature overn igh t. Th e resin
was wash ed th ree tim es with NMP, th ree tim es with DCM, th ree tim es with MeOH.
Cyclization to 2-(Arylam in o)ben zim idazoles (Resin 29)
A polypropylen e 10-m l fritted syrin ge was ch arged with ≈500 m g of resin 28 an d th e resin
was wash ed th ree tim es with NMP. A 1 M solution (5 m l) of DIC in NMP was added, an d th e
reaction was carried out at am bien t tem perature overn igh t. Th e resin was wash ed th ree
tim es with NMP, th ree tim es with DCM, th ree tim es with MeOH.
Alkylation of Ben zim idazole (Resin s 31 an d 32)
Procedure A: A polypropylen e 5-m l fritted syrin ge was ch arged with 100 m g of resin 29,
th e resin was wash ed th ree tim es with dry DMF, an d 50 m g of an h ydrous K CO an d 2 m l
2
3
of a 1 M solution of an electroph ile in DMF were added. Th e syrin ge was sh aken in an in cu-
Collect. Czech. Chem. Commun. (Vol. 66) (2001)