Thioxopyrimidine in Heterocyclic Synthesis III: Synthesis and Properties of Some Novel Heterocyclic Chalcone Derivatives Containing a Thieno[2,3-d]pyrimidine-Based Chromophore
Table 2
Spectra data of 6-(3-substituted-acryloyl)-5-(1-pyrrolyl)-4-methyl-2-phenyl-thieno[2,3-d]pyrimidine derivatives 6a–n.
MS
IR
1H-NMRa
Dye
(m/e M+)
(KBr)
(CF3COOD)
(cm−1)
(ppm)
6a
455.5
1667 (CO)
2.20 (3H, s, CH3), 5.80 (1H, d, , COCH), 6.62 (2H, m, 3,4-H of pyrrolyl), 6.87 (2H, m, 2,5-H of pyrrolyl), 6.75 (2H, d, , 3,5-H of phenyl), 7.33 (2H, d, , 2,6-H of phenyl), 7.82 (1H, d, , CH–), 8.57–8.55, 7.55–7.21 (5H, m, phenyl-H)
6b
464
1628 (CO)
2.27 (3H, s, CH3), 3.06 (6H, s, N(CH3)2), 5.70 (1H, d, , COCH), 6.59–6.50 (2H, m, 3,4-H of pyrrolyl), 6.98–6.87 (2H, m, 2,5-H of pyrrolyl), 6.70 (2H, d, , 3,5-H of phenyl), 7.25 (2H, d, , 2,6-H of phenyl), 7.75 (1H, d, , CH–), 8.57–8.54, 7.51–7.50 (5H, m, phenyl-H).
6c
435
1663 (CO)
2.27 (3H, s, CH3), 2.39 (3H, s, CH3), 6.02 (1H, d, , COCH), 6.61–6.51 (2H, m, 3,4-H of pyrrolyl), 7.09–6.87 (2H, m, 2,5-H of pyrrolyl), 7.79 (1H, d, , CH–), 8.59–8.58, 7.81–7.33 (9H, m, phenyl-H).
6d
451
1668 (CO)
2.33 (3H, s, CH3), 3.84 (3H, s, OCH3), 5.75 (1H, d, , COCH), 6.60 (2H, t, 3,4-H of pyrrolyl), 6.87 (2H, d, , 3,5-H of phenyl), 6.99 (2H, t, 2,5-H of pyrrolyl), 7.28 (2H, d, , 2,6-H of phenyl), 7.76 (1H, d, , CH–), 8.59–8.55, 7.52–7.51 (5H, m, phenyl-H).
6e
492
1628 (CO)
1.21 (6H, t, , CH3), 2.27 (3H, s, CH3), 3.41 (4H, q, , CH2), 5.68 (1H, d, , COCH), 6.59–6.49 (4H, m, 3,4-H of pyrrolyl and 3,5-H of phenyl), 6.98–6.87 (2H, m, 2,5-H of pyrrolyl), 7.24 (2H, d, , 2,6-H of phenyl), 7.74 (1H, d, , CH–), 8.56–8.53, 7.50–7.49 (5H, m, phenyl-H).
6f
497
1667 (CO)
2.18 (3H, s, CH3), 5.75 (1H, d, , COCH), 6.50 (2H, t, 3,4-H of pyrrolyl), 6.86 (2H, t, 2,5-H of pyrrolyl), 8.65–8.54, 7.63–7.38 (15H, m, CH– and phenyl-H).
6g
411
1667 (CO)
2.28 (3H, s, CH3), 5.88 (1H, d, , COCH), 6.59–6.48 (3H, m, 3,4-H of pyrrolyl and 4-H of furyl), 6.87 (2H, m, 2,5-H of pyrrolyl), 7.00 (1H, d, , 3-H of furyl), 8.15 (1H, d, , CH–), 8.63–8.54, 7.58–7.48 (6H, m, 5-H of furyl and phenyl-H).
6h
427
1641 (CO)
2.11 (3H, s, CH3), 5.47 (1H, d, , COCH), 6.63–6.39 (3H, m, 3,4-H of pyrrolyl and 4-H of thienyl), 7.06–7.03 (2H, m, 2,5-H of pyrrolyl), 7.13 (1H, d, , 3-H of thienyl), 7.80 (1H, d, , CH–), 8.48–8.45, 7.54–7.44 (6H, m, 5-H of thienyl and phenyl-H).
6i
545
1623 (CO)
2.06 (3H, s, CH3), 5.79 (1H, d, , COCH), 6.51 (2H, m, 3,4-H of pyrrolyl), 6.90 (2H, m, 2,5-H of pyrrolyl), 8.62–8.42, 8.32–8.05 (15H, m, CH–, phenyl-H and pyrenyl-H).
6j
538
1633 (CO)
1.77 (3H, t, , CH3), 2.52 (3H, s, CH3), 4.03 (2H, d, , CH2), 5.79 (1H, d, , COCH), 6.51 (2H, m, 3,4-H of pyrrolyl), 6.90 (2H, m, 2,5-H of pyrrolyl), 8.72–7.61, (13H, m, CH–, phenyl-H and carbazolyl-H).
6k
463
1643 (CO)
2.10 (3H, s, CH3), 2.22 (6H, s, CH3), 2.28 (3H, s, CH3), 5.88 (1H, d, , COCH), 6.51–6.45 (2H, m, 3,4-H of pyrrolyl), 6.88–6.84 (2H, m, 2,5-H of pyrrolyl), 7.39 (1H, d, , CH–), 8.58–8.53, 7.54–7.51 (7H, m, phenyl-H).
6l
478
3324 (NH), 1622 (CO)
2.06 (3H, s, CH3), 2.16 (3H, s, COCH3), 5.78 (1H, d, , COCH), 6.49 (2H, m, 3,4-H of pyrrolyl), 6.97 (2H, m, 2,5-H of pyrrolyl), 6.87 (2H, d, , 3,5-H of phenyl), 7.57 (1H, d, , CH–), 8.50–8.29, 7.47–7.41 (7H, m, phenyl-H), 8.29 (1H, br, NH).
6m
521
1679 (CO)
2.22 (3H, s, CH3), 6.13 (1H, d, , COCH), 6.24 (2H, m, 3,4-H of pyrrolyl), 6.91 (2H, m, 2,5-H of pyrrolyl), 8.93–7.99, 7.54–7.26 (15H, m, CH–, phenyl-H and anthracenyl-H).
6n
588
1631 (CO)
2.30 (3H, s, CH3), 5.71 (1H, d, , COCH), 6.55 (2H, t, 3,4-H of pyrrolyl), 6.98–6.94 (4H, m, 3,5-H of phenyl and 2,5-H of pyrrolyl), 7.74 (1H, d, , CH–), 8.59–8.57, 7.53–7.13 (17H, m, phenyl-H).
