48 Abaee et al.
1H NMR (CDCl3): δ 3.78 (s, 4H), 7.20–7.40 (m, 8H),
7.62 (s, 2H); 13C NMR (CDCl3) δ 30.0, 129.0, 131.3,
133.5, 134.2, 135.1, 135.7, 188.5; MS (70 eV) m/z
(%): 360 (M+., 10), 147 (37), 115 (100).
importantly, presenting the most versatile and effi-
cient method for double crossed aldol condensation
of heterocyclic ketones makes this protocol an at-
tractive addition to the present literature archive.
Application of this procedure to other heterocyclic
systems and homocyclic ketones is currently under
investigation and will be reported in due course.
(3Z,5Z)-Tetrahydro-3,5-bis((E)-3-phenylallylide-
ne)thiopyran-4-one (2e) [3]. Brown crystals were
obtained in 88% yield, mp 202–204◦C; UV (CH2Cl2,
nm) λmax 380; IR (KBr, cm−1) 1645, 1609, 1577, 1287;
1H NMR (CDCl3) δ 3.75 (s, 4H), 6.80–7.80 (m, 16H);
13C NMR (CDCl3) δ 28.5, 122.6, 127.3, 128.8, 129.2,
136.1, 141.9; MS (70 eV) m/z (%) 344 (M+., 31), 253
(19), 141 (97), 115 (100).
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nm) λmax 372; IR (KBr, cm−1) 1648, 1471, 1284, 747;
1H NMR (CDCl3) δ 4.04 (s, 4H), 6.40–6.58 (m, 4H),
7.35–7.49 (m, 4H); 13C NMR (CDCl3): δ 29.7, 112.3,
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(3Z,5Z)-Tetrahydro-3,5-bis((thiophen-2-yl)methy-
lene)thiopyran-4-one (2g) [3]. Yellow crystals were
obtained in 86% yield, mp 155–157◦C; UV (CH2Cl2,
1
nm) λmax 365; IR (KBr, cm−1) 1646, 1582, 1281; H
NMR (CDCl3) δ 3.90 (s, 4H), 7.00–7.50 (m, 6H),
7.86 (s, 2H); 13C NMR (CDCl3) δ 29.5, 127.6, 129.4,
133.2, 138.3, 187.0; MS (70 eV) m/z (%) 304 (M+.,
15), 153 (49), 122 (100), 121 (100). Anal. Calcd for
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(3Z,5Z)-Tetrahydro-3,5-bis((pyridine-3-yl)methyl-
ene)thiopyran-4-one (2h) [3]. Yellow crystals were
obtained in 81% yield, mp 186–188◦C; UV (CH2Cl2,
1
nm) λmax 301; IR (KBr, cm−1) 1723, 1557, 1273; H
NMR (CDCl3) δ 3.78 (s, 4H), 7.10–7.60 (m, 8H), 8.51
(s, 2H); 13C NMR (CDCl3) δ 29.7, 123.2, 130.7, 133.0,
136.0, 136.6, 149.4, 150.3, 185.0; MS (70 eV) m/z
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CONCLUSIONS
We have established a general and efficient syn-
thetic methodology for the preparation of 3,5-
bisarylmethylidenes of heterocyclic ketones at room
temperature by using an efficient medium consisted
of magnesium bromide diethyl etherate, triethy-
lamine, and methanol. In comparison with the pre-
vious procedures, the present methodology is very
mild and fast. Use of no solvent, ease of opera-
tion, no special handling requirements, and more
Heteroatom Chemistry DOI 10.1002/hc