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Please login to access the full content or check if you have access via14.4.4.1.1.1.1.1 Variation 1: Direct Conversion of 4H-1-Benzopyran-4-ones into 4H-1-Benzopyran-4-thiones
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Williams, A. C.; Camp, N., Science of Synthesis, (2003) 14, 533.
This method has proved suitable for the preparation of simple 4H-1-benzopyran-4-thiones (e.g., 567, 568),[785,792,797] benzo- and furo-fused derivatives,[795,796] as well as a range of more highly substituted 2-aryl- and 3-aryl-4H-1-benzopyran-4-ones (e.g., 569, 570) (Scheme 183).[798–800] The procedure involves heating the substrate and Lawesson's reagent together in a suitable solvent, typically dry toluene, but xylene and benzene have also been used. The products are isolated by chromatography and/or recrystallization from a suitable solvent after removal of the reaction solvent. Microwave heating of mixtures of solid substrates and Lawesson's reagent obviates the necessity for solvent and greatly reduces reaction times.[405]
Meeeee 888 Meeeee Meeeeeeeee ee 8M-8-Meeeeeeeee-8-eeee eeee 8M-8-Meeeeeeeee-8-eeeeeee Meeee Meeeeeee'e Meeeeee[888,888,888,888,888]
Mee eeeee eeeeee eeee eeeeeeeeee eeeeeee ee eeeeeeeeee eeeeeeeeeeee. Mee eeeee ee eeeeeeeeee eeeeeeeeee eeeeee ee eeee eeeeeee ee eeee eee Meeeeeee'e eeeeeee (Meeeee 888), eeeeeee, eeeee eee eeeeeeeee eeeeeeee eee eeeeee eeeeeeeeee eeeeee eeee eeee ee eeeeeeeee eeee eeeee eeee eeeeeee eeeee eeee-eeeeeeeee eeeeeeeee eee ee eeeeeeee: eee eeeeeeeee ee eee eeeeee eeeeeee ee eeeee eeee eeeeeeeeee eeeeeeeeeee. Meeeeeeeee eeeeeeeeeeee eee eeee eeee eee eee eeeeeeeeeee ee eeeeee eeeeeeeeeee 8M-8-eeeeeeeeee-8-eeeeeee 888,[888,888] ee eeee ee eeeee eeeee ee eeeee eeee eeeeeee (eeeeee, eeeeee, eeeeeeeeee, eee eeeeeeeeeeeeee),[888] eee eeeeeeeeeee 8-eeee-8M-8-eeeeeeeeee-8-eeee 888.[888,888]
Meeeee 888 Meeeee Meeeeeeeee ee 8M-8-Meeeeeeeee-8-eeee eeee 8M-8-Meeeeeeeee-8-eeeeeee eeeee Meeeeeeeee Meeeeeeeeeee[888,888,888,888,888,888–888]
Meeeeeeeeeee Meeeeeeeee
8-(Meeeeeeeeeeee)-8-eeeeee-8M-8-eeeeeeeeee-8-eeeeee (888):[888]
M eeeeeee ee 8-(eeeeeeeeeeeee)-8-eeeeee-8M-8-eeeeeeeeee-8-eee (88.8 e, 8.8888 eee) eee Meeeeeee'e eeeeeee (88.8 e, 8.8888 eee) ee eeeeee (888 eM) eee eeeeeee ee 88°M eee 88 eee. Meeee eeeeeee ee ee, eee eeeeeeeeeee eee eeeeeeee eee eee eeeeeeee eeeeeeeeee ee eeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MMMe8) eeeeeeee ee eeeeeeeeeeeeeeeee (MeMM) ee eeee eee eeeeeeee; eeeee: 88.8 e (88%); ee 888°M.
8-(8-Meeee)-8M-8-eeeeeeeeee-8-eeeeee (888, M8 = 8-Mee; M8 = M); Meeeeee Meeeeeeee:[888]
M eeeeeee ee 8-(8-eeeee)-8M-8-eeeeeeeeee-8-eee (8.88 e, 8 eeee), Meeeeeee'e eeeeeee (8.88 e, 8 eeee), eee eee eeeeeee (88 eM) eee eeeeee eeeee eeeeee eee 8 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eeeeeeeeeeeeee (MeMM) ee eeee eeeeee eeeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
8-Meeeeee-8-(8-eeeeeeeeeeeee)-8M-8-eeeeeeeeee-8-eeeeee (888, M8 = MMe; M8 = MMe); Meeeeee Meeeeeeee:[888]
Me eeeeeeee eeeeeee ee 8-eeeeeee-8-(8-eeeeeeeeeeeee)-8M-8-eeeeeeeeee-8-eee (888 ee, 8 eeee) eee Meeeeeee'e eeeeeee (888 ee, 8.8 eeee) eee eeeeee ee e eeeee eeee, eeeee eee eeee eeeeee ee ee eeeeeee eeee eeeeee e eeeeeeee eeeeeeeee eeee (888 M) eee eeeeeeeeee eee 8 eee: eee eeeeeeee ee eee eeeeeeee eee eeeeeeeee ee MMM eeeeeeeeeee. Meee eeeeeeeeee eee eeeeeee eee eeeeeeeee ee MM8Me8, eeeeeeee ee eeeeee eee, eee eeeeee eeeee eeee eeeeee, eeee MeMMe/eeeeee (8:8) ee eeeeee eee eeeeeee; eeeee: 888 ee (88%).
8-(Meeeeeeeeeee)-8-eeeeeee-8M-8-eeeeeeeeee-8-eeeeee (888, M8 = M8 = M8 = M; M8 = MMe; M8 = MMe8); Meeeeee Meeeeeeee:[888]
M eeeeeee ee 8-(eeeeeeeeeeee)-8-eeeeeee-8M-8-eeeeeeeeee-8-eee (8 e, 8 eeee) eee M8M8 (8 e, 8 eeee) ee eee eeeeeeee (88 eM) eee eeeeee eeeee eeeeee eee 8 e eeee eeeeee eeee eeeeeee eee. Mee eeeeeeeeeee eee eeeeeeeee, eeeeee eeee M8M eee eeeeeeeeeeeeee (MeMM) ee eeee e eeeeee eeeee; eeeee: 8.8 e (88%); ee 888–888°M.
Meeee [8-(8-Meeeee-8M-8-eeeeeeeeee-8-ee)eeeeee]eeeeeee (888, M8 = M8 = M8 = M8 = M; M8 = Me); Meeeeee Meeeeeeee:[888]
Meeee [8-(8-eee-8M-8-eeeeeeeeee-8-ee)eeeeee]eeeeeee (8 e, 8.8 eeee) eee eeeeeeeee ee eeeeeeee (88 eM) eee eeeeeee eeee M8M8 (8 e, 8.8 eeee). Mee eeeeeee eee eeeeee eeeee eeeeee eee 8 e eeee eeeeee eee eeeeee eeee eeee M8M, eeeeeeee eeeeeeeeee. Mee eeeeee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeeeeeee (MeMM); eeeee: 8.8 e (88%); ee 88–88°M.
References
[311] | Meeeee, M.; Meeeeeeeeeee, M.; Meeeee, M.; Meee, M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[405] | Meeee, M. M.; Meeee, M., Mee. Meee., (8888) 8, 888. |
[440] | Meeeee, M. M.; Meee, Me. Me'.; Meeeeeeeeee, M.; Meeeeee, M. M.; Meeee, M. M.; Meeeeeee, M. M.; Meeeee, M., Meee. Meeeeeeeeee. Meeeee., (8888), 888; Meee. Meeeeeeeee. Meeee. (Meee. Meeeee.), (8888) 88, 888. |
[536] | Meeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M. M., Mee. Meee. Meee., (8888) 88, 8888. |
[785] | Meee, M.; Meeeeeeee, M.; Meeeeee, M. M.; Meeeee, M. M., Meee. Mee. Meee. Me., (8888) 888, 888. |
[792] | Meee, M.; Meeee, M.; Meeeeeee, M., Meeeeeeee, (8888), 888. |
[793] | Meeeee, M.; Meeeeeeeeeee, M.; Me Meeeeee, M.; Meeee, M.; Meeeeeee, M.; Meeee, M.; Meeeeee, M., Mee. M. Mee. Meee., (8888) 88, 888. |
[794] | Meeeeee, M.; Meeeee, M.; Meeeee-Meeee, M., Meeeee M. Meee., Meee. M, (8888) 88, 88. |
[795] | Meeee, M. M.; Me-Meeeeeeee, M. M.; Meeeee, M. M., Meeeeeeeee, Meeeee Meeeeee Meeee. Meee., (8888) 88, 888. |
[796] | Meeee, M. M., Meeeeeeeee, Meeeee Meeeeee Meeee. Meee., (8888) 88, 888. |
[797] | Meeeee, M. M.; Meeeee, M. M.; Meeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[798] | Meeee, M., Meeeeeeeee. Meeeee., (8888) 8, 888. |
[799] | Meeee, M.; Meeee, M., M. Meee. Mee., Meeee., (8888), 888. |
[800] | Meeee, M., M. Meee. Mee., Meeee., (8888), 888. |
[801] | Meeeeee, M. M.; Meeeee, M. M., Meeeeeeeee, Meeeee Meeeeee Meeee. Meee., (8888) 88, 888. |
[802] | Meeee, M.; Meeeee, M.; Meee, M.; Meeeee, M., Meeeeee, Me. Mee., (8888) 88, 888. |
[803] | Meeee, M.; Meee, M. M., M. Meee. Mee., (8888), 8888. |
[804] | Meeeeee, M. M.; Meeeeee, M. M.; Meeeee, M. M., Meeeeeeeee, Meeeee Meeeeee Meeee. Meee., (8888) 88, 888. |
[805] | Meeeeeeeeee, M., Meee. Meeee. (Meeeeeee, Mee.), (8888) 888, 88. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8, 888.