Journal of Sulfur Chemistry 411
4.2.5. Ethyl 2-(3-amino-2-(cyclopentylidenehydrazono)-4-oxothiazolidin-5-ylidene)
acetate (5e)
1H-NMR (CDCl3/TMS) δ (ppm), J (Hz): 6.88 (s, 1H, CH); 4.78 (sbr, 2H, NH2); 4.28 (q, J3 = 7.1,
2H, CH2); 2.60–2.09 (m, 8H, CH2); 1.33 (t, J3 = 7.1, 3H, CH3). 13C-NMR (CDCl3/TMS) δ
(ppm): 181.5; 165.7; 162.0; 154.2; 139.7; 116.8; 61.6; 33.5; 30.4; 24.8; 25.7; 14.2. Ms (m/z,
rel. int. (%)): 296 (M+, 100); 280 (M+–NH2, 11); 267 (M+–C2H5, 25); 214 (M+–C5H8N, 35);
169 (M+–C6H7O3, 20). IR (cm−1) KBr disc: 3327 (N–H), 1700 (C O). Yellowish solid, m.p.
=
123–126◦C, yield (72%).
4.2.6. Ethyl 2-(6ꢀ-oxospiro[cyclopentane-1,3ꢀ-thiazolo[3,2-b][1,2,4,5]tetrazine]-
7ꢀ(2ꢀH,4ꢀH,6ꢀH)-ylidene)acetate (5f)
1H-NMR (CDCl3/TMS) δ (ppm), J (Hz): 6.89 (s, 1H, CH); 5.57 (s, 1H, NH); 4.52 (s, 1H, NH);
4.29 (q, J3 = 7.1, 2H, CH2); 1.73–1.50 (m, 10H, CH2); 1.32 (t, J3 = 7.1, 3H, CH3). 13C-NMR
(CDCl3/TMS) δ (ppm): 166.2; 159.1; 140.6; 134.6; 115.3; 66.7; 61.5; 32.0; 25.4; 21.8; 14.2.
Ms (m/z, rel. int. (%)): 310 (M+, 100); 294 (M+–O, 10); 237 (M+–C3H5O2, 13); 214 (M+–
◦
C6H10N, 20). IR (cm−1) KBr disc: 3326 (N–H), 1706 (C O). Yellowish solid, m.p. 166–168 C,
yield (88%).
=
4.2.7. Ethyl 2-(3-amino-2-(cycloheptylidenehydrazono)-4-oxothiazolidin-5-ylidene)
acetate (5g)
1H-NMR (CDCl3/TMS) δ (ppm), J (Hz): 6.89 (s, 1H, CH); 4.80 (sbr, 2H, NH); 4.50 (q, J3 = 7.1,
2H, CH2); 2.65 (m, 4H, CH2); 2.01–1.30 (m, 8H, CH2); 1.30 (t, J3 = 7.1, 3H, CH3). 13C-NMR
(CDCl3/TMS) δ (ppm): 181.5; 165.7; 162.0; 154.1; 139.7; 116.9; 61.6; 33.5; 30.4; 24.8; 14.2.
Ms (m/z, rel. int. (%)): 324 (M+, 1); 230 (M+–C7H12, 100); 202 (M+–C7H12N2, 57); 214 (M+–
◦
C7H14N3, 53). IR (cm−1) KBr disc: 3323 (N–H), 1719 (C O).Yellowish solid, m.p. 126–130 C,
yield (75%).
=
Acknowledgements
Deanship of research and graduate studies atYarmouk University is acknowledged for the financial support. Professor Dr
Peter Langer of University of Rostock is highly acknowledged for providing laboratory facilities.
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