Synthesis and kinetic studies of a simple prostacyclin model

Abstract

4-Phenyl-4-methyl-2,2-dibutyl-1,3,2-dioxastannolane (4). The racemic compound was prepared from a commercial diol (Janssen, >98%; mp 44-45 °C), purified by crystallization; the 42% ee sample was prepared from an enriched diol, obtained following a known procedure:20 mp 93-95 °C. 13C NMR: Ph,

Investigations into a mild Diels-Alder approach to 6-substituted quinazoline-2,4-dione derivatives

“…Diels-Alder adduct 4a (0.80 g, 1.75 mmol) was dehydrated with concentrated sulfuric acid (8 mL) as described for Table II, entry 1. The product was recrystallized from 2-propanol to give a colorless solid, 0.56 g (73%): mp 176-177 °C; IR 1724, 1665, 1656, 1597, and 1502 cm'1; MS m/z 439 (MH+); >H NMR (DMSO-d6) 8 2.57-2.70 (m, 6 H), 2.90-3.00 (m, 4 H), 3.77 (s, 3 H), 3.90 (s, 3 H), 4.07 (t, J = 6.7 Hz, 2 H), 6.85-6.98 (m, 4 H), 7.71 (dd, J = 1.3 Hz and J = 8.2 Hz, 1 H), 7.77 (d, J = 1.3 Hz, 1 H), 8.06 (d, J = 8.2 Hz, 1 H), and 11.64 (br s, 1 H, exchanges with D20); HRMS calcd for C23H26N405 (M+) 438.1903, found 438.1905. Anal.…”

“…3.76 (s, 3 H), 4.10-4.15 (m, 2 H), 6.85-6.97 (m, 4 H), 7.70 (d, J = 8.9 Hz, 1 H), 8.24 (dd, J = 2.3 Hz and J = 8.9 Hz, 1 H), and 8.49 (d, J = 2.3 Hz, 1 H); (7-methylsulfonyl) b 2.55-2.65 (m, 6 H), 2.90-2.97 (m, 4 H), 3.36 (s, 3 H), 3.57 (s, 3 H), 3.76 (s, 3 H), 4.10-4.15 (m, 2 H), 6.85-6.97 (m, 4 H), 7.80 (dd, J = 1.4 Hz and J = 8.2 Hz, 1 H), 7.88 (d, J = 1. 4 Hz, 1 H), and 8.28 (d, J = 8.2 Hz, 1 H); HRMS calcd for C23H28N4OsS (M+) 472.1780, found 472.1782.…”

Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties

“…etc.). QPSs were obtained using this method from triphenylphosphine for n = 1 [39,40], 2 , 3 [39,40,45,47,[60][61][62][63][64][65][66][67][68][69][70], 4 [40,44,47,62,65,[71][72][73][74][75][76][77][78][79][80][81][82][83][84], 5 [45,55,61,62,65,67,[85][86][87][88][89][90][91][92][93][94]…”

Studies on sulfinatodehalogenation: XVIII. The reaction of perfluoroalkyl iodides with α‐methylene cyclic ethers

“…The formation of all the above products can be readily explained through the hydrolysis of the primary adducts of perfluoroalkyl iodides to the exocyclic olefinic bond of cyclic ether, such as 9, followed by ring opening. 9 We have also studied the reaction of a-methylene-tetrahydrofuran (lo),' which gave 8 tautomeric mixture of Ila and 12a or lld and 12d in high yield as indicated by NMR analysis.a1m…”