. 2011 Mar 9;16(3):2304–2312. doi: 10.3390/molecules16032304

Table 2.

IR and ¹H-NMR spectral data of compounds 2a–f, 3a–f, 4a–f and 5a–c.

Compound	IR cm⁻¹ (KBr)				¹H NMR (δ / ppm)^a
	C=C	C=N	C=O	NH	Ar–H’s and = C–CH=CH (m)	=C–CH=CH (d), J =12 Hz	Pyrazole-C₄–H (s) or isoxazole–C₄–H (s)	NH (s)	Cyclopropyl ring H’s		Ar–CH₃ (s) Ar–OCH₃ and CH₃CO–
	C=C	C=N	C=O	NH	Ar–H’s and = C–CH=CH (m)	=C–CH=CH (d), J =12 Hz	Pyrazole-C₄–H (s) or isoxazole–C₄–H (s)	NH (s)	CH (m)	2 (CH₂) (m)	Ar–CH₃ (s) Ar–OCH₃ and CH₃CO–
2a	1592	1629	1678	3420	7.36–7.91	6.72	―	10.66	1.91–2.55	0.75–1.37	2.21
2b	1617	1647	1698	3390	7.23–8.45	6.93	―	10.45	1.80–2.64	0.71–1.40	―
2c	1582	1616	1664	3330	7.19–7.63	6.60	―	9.97	1.82–2.49	0.78–1.29	―
2d	1587	1636	1669	3336	7.29–7.82	6.71	―	10.82	1.71–2.36	0.70–1.40	2.10
2e	1601	1628	1687	3411	7.20–7.71	6.75	―	10.73	1.63–2.40	0.77–1.46	2.19, 3.49
2f	1617	1644	1681	3332	7.17–7.49	6.95	―	9.99	1.56–2.59	0.78–1.16	3.42
3a	1519	1629	1670	―	7.26–7.92 ^b	―	6.85	―	1.90–2.48	0.69–1.21	2.13
3b	1586	1633	1684	―	7.24–8.33 ^b	―	7.12	―	1.76–2.66	0.80–1.36	―
3c	1556	1641	1660	―	7.22–7.71 ^b	―	6.78	―	1.73–2.40	0.71–1.28	―
3d	1590	1644	1678	―	7.24–7.77 ^b	―	6.64	―	1.75–2.41	0.77–1.33	2.11
3e	1571	1623	1686	―	7.21–7.68 ^b	―	6.69	―	1.66–2.39	0.71–1.33	2.10,3.44
3f	1596	1633	1664	―	7.11–7.62 ^b	―	6.74	―	1.49–2.55	0.77–1.19	3.39
4a	1587	1645	1669	―	7.18–7.79 ^b	―	―	―	1.92–2.41	0.67–1.32	2.01, 2.16
4b	1610	1646	1667	―	7.22–8.22 ^b	―	―	―	1.70–2.66	0.71–1.40	2.13
4c	1602	1626	1669	―	7.16–7.75 ^b	―	―	―	1.68–2.39	0.75–1.26	2.11
4d	1594	1630	1670	―	7.33–7.76 ^b	―	―	―	1.73–2.44	0.71–1.38	1.99, 2.13
4e	1600	1633	1677	―	7.26–7.72 ^b	―	―	―	1.60–2.47	0.71–1.26	2.13,3.32,2.15
4f	1615	1646	1671	―	7.25–7.51 ^b	―	―	―	1.47–2.61	0.76–1.33	3.34,2.10
5a	1580	1627	―	―	7.19–7.99 ^b	―	5.69	―	1.82–2.51	0.71–1.36	―
5b	1571	1629	―	―	7.22–7.62 ^b	―	5.42	―	1.43–2.45	0.69–1.27	―
5c	1569	1633	―	―	7.26–7.70 ^b	―	5.46	―	1.57–2.41	0.67–1.29	3.30

^a Solution in DMSO-d₆; ^b The chemical shift only indicates Ar–H’s.