| Original language | English (US) |
|---|---|
| Pages (from-to) | 716-719 |
| Number of pages | 4 |
| Journal | Organic Preparations and Procedures International |
| Volume | 30 |
| Issue number | 6 |
| DOIs | |
| State | Published - Dec 1998 |
| Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry
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In: Organic Preparations and Procedures International, Vol. 30, No. 6, 12.1998, p. 716-719.
Research output: Contribution to journal › Article › peer-review
}
TY - JOUR
T1 - A facile synthesis of new 2-phosphonobenzyloxy-1, 3, 2-benzoxaza(dioxa or diaza)phospholes
AU - Zhou, Jia
AU - Chen, Ruyu
N1 - Funding Information: distilled off, and purification of the product was achieved with silica gel flash column chromatography using ethyl acetatdpetroleum ether (bp. 60-90") (1:4, v/v) as the eluent. This afforded 6a as a colorless syrup (1.02 g, 79%). IR (film): 3190, 3031, 2909, 1602, 1499,1465, 1253 (s, P=O), 1053, 1016, 944,881 (s, P-0-C), 830 (m),7 54 (s), 714 (m, P=S) cm-'; 'H NMR (CDCI,): 6 1.23 (t, 6 H, 2 CH,), 2.28 (ds, 3 H, CH,), 4.07 (m, 4 H, 2 CH,), 5.67 (dd, 1 H, CH, J = 14.0 Hz),6 .71-7.33 (m, 8 H, 2 C6H4);, 'P NMR (CDCl,); 6 15.77, 16.17,69.69,69.29 (two signals overlapped), 68.89, ,JPlp2=3 2.34 Hz; MS (EI) d z : 428 (M+4,.9 6%), 213 (15.1), 171 (13.09), 139 (12.82), 119 (24.49), 111 (17.24), 105 (loo), 93 (22.26), 91 (35.67), 77 (14.9), 65(26.16). Anal. Calcd for C,,H,,O,P,S: C, 50.46; H, 5.19. Found: C, 50.61; H, 5.42 2-[(P,P-Diethoxy)phosphono(p-methyl)be~yloxy]-l~~-be~~~aphos2p-hSuollfeid e (6b).- A colorless syrup; yield 87%. IR (film): 3388, 3127, 2971, 1607, 1511, 1490 (s), 1251 (s, P=O), 1091, 1049, 1015, 918 (s, P-0-C, P-N, C-N), 831 (s), 734 (s), 698 (s, P=S) cm-'; 'H NMR (CDCI,): 6 1.22 (m, 6 H, 2 CH,), 2.34 (ds, 3 H, CH,), 3.92-4.18 (m, 4 H, 2 CH,), 5.76 (dd, 1 H, CH, J = 12.6 Hz),5 .78 (d, 1 H, NH, J = 18 Hz),6 .14 (d, 1 H, NH,J = 18 Hz), 6.68-7.36 (m, 8 H, 2 C6H4)., 'P NMR (CDC1,): 6 17.36, 16.69, 70.94, 70.27, ,JPlp2= 24.25 Hz; MS (EI) d z : 426 (M+,19 .12%), 290 (4.79), 242 (10.93), 213 (11.99), 185 (16.07), 169 (10.37), 154 (21.10), 137 (34.3), 119 (11.77), 109 (5.09), 105 (loo), 93 (16.75), 91 (22.07), 65 (21.55). Anal. Calcdfor C,,H,N,O,P,S: C, 50.70; H, 5.68; N, 6.57. Found: C, 50.98; H, 5.61; N, 6.86 2-[(P,P-Diethoxy)phosphono(p-methyl)be~ylo~]-l~,2-be~ox~aphos2p-Shuolflied e (6c).- A colorless syrup; yield 82%. JR (film): 3407 (m, N-H), 2969, 1617, 1588, 1502, 1458 (s), 1252 (s, P=O), 1182,1054,1021,953,923 (s, P-0-C, P-N, C-N), 848 (s), 745 (s), 710 (s, P=S) cm-'; 'H NMR (CDCI,): 6 1.16 (m, 6 H, 2 CH,), 2.32 (ds, 3 H, CH,), 2.83-4.52 (m, 4 H, 2 CH,), 5.58-5.92 (dq, 1 H, CH, J = 14.0 Hz), 6.54-6.83 (dd, 1 H, NH, J = 18.3 Hz), 6.63-7.42 (m, 8 H, 2 C6H4); ,'P NMR (CDCI,): 6 17.54 (d), 17.47 (d), 74.02 (d), 73.34 (d), 'JPlp2= 42.22 Hz;M S (EI) dz: 427 (M+, 8.42%), 392 (25.87), 364 (39.42), 272 (14.49), 241 (11.69), 213 (42.16), 180 (26.78), 138 (13.0), 121 (30.97), 108 (56.04), 105 (loo), 93 (29.78),9 1 (21.71), 80 (41.97), 74 (24.40), 65 (29.24). Anal. Calcd for C,,H,,NO,P,S: C, 50.58; H, 5.44; N, 3.28. Found C, 50.39; H, 5.52; N, 3.41 2-[(P,P-Diethoxy)phosphono~-chloro)be~yloxy]-l~~-be~~~ph2o-Ssuplhfiodele (a d).- A colorless syrup; yield 87%. IR (film): 3380 (s, MI), 3123,2964, 1628, 1602, 1488 (s), 1247 (s, P=O), 1083,1011,971,918 (s, P-0-C, P-N, C-N), 827 (s), 733 (s), 709 (s, P=S) cm-'; 'H NMR (CDCI,): 6 1.17-1.34 (m, 6 H, 2 CH,), 3.96-4.17 (m, 4 H, 2 CH,), 5.79 (dd, 1 H, CH, J = 12.52 Hz),5 .82 (d, 1 H, NH, J = 20.84 Hz), 6.21 (d, 1 H, NH,J = 18.78 Hz), 6.68-7.42 (m, 8 H, 2 C6H4);3 1PN MR (CDCI,): 6 16.90, 16.61, 71.10, 70.81, 'J,,,, = 23.50 Hz; MS (EI) d z : 446 (M+, 29.24%), 290 (5.84), 262 (24.11), 233 (10.85), 206 (16.09), 185 (13.34), 169 (23.05), 154 (90.20), 137 (54.73), 127 (31.86), 125 (loo), 121 (10.50), 105 (18.89), 93 (13.45), 77 (16.47), 65 (24.00). Anal. Calcd for C,,H,,ClN,O,P,S: C, 45.69; H, 4.75; N, 6.27. Found: C, 45.53; H, 4.62; N, 6.53 Acknowledgement- The authors thank the National Natural Science Foundation of China for financial support.
PY - 1998/12
Y1 - 1998/12
UR - http://www.scopus.com/inward/record.url?scp=0042352680&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0042352680&partnerID=8YFLogxK
U2 - 10.1080/00304949809355332
DO - 10.1080/00304949809355332
M3 - Article
AN - SCOPUS:0042352680
SN - 0030-4948
VL - 30
SP - 716
EP - 719
JO - Organic Preparations and Procedures International
JF - Organic Preparations and Procedures International
IS - 6
ER -