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25
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77951686262
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The 2- and 3-amines derived from electron-rich, fivemembered heteroaromatic compounds usually are highly unstable compounds, unless electron-withdrawing substituents are present, and therefore find uncommon use in synthetic annulation processes.
-
The 2- and 3-amines derived from electron-rich, fivemembered heteroaromatic compounds usually are highly unstable compounds, unless electron-withdrawing substituents are present, and therefore find uncommon use in synthetic annulation processes.
-
-
-
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26
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0009905231
-
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Tricycle 3a was originally reported in low yield via a troublesome six-step sequence from an N-(aryloxy)pyridinium salt, see
-
Tricycle 3a was originally reported in low yield via a troublesome six-step sequence from an N-(aryloxy)pyridinium salt, see: Abramovitch, R. A.; Inbasekaran, M. N.; Kato, S.; Radzikowska, T. A.; Tomask, P. J. Org. Chem. 1983, 48, 690.
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27
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0000416574
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For leading reviews on the chemistry of iminophosphoranes and their use in aza-Wittig electrocyclization reactions, see: (a)
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For leading reviews on the chemistry of iminophosphoranes and their use in aza-Wittig electrocyclization reactions, see: (a) Wamhoff, H.; Richard, G.; Stolben, S. Adv. Heterocycl. Chem. 1995, 64, 159.
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(a) Degl'Innocenti, A.; Funicello, M.; Scafato, P.; Spagnolo, P.; Zanirato, P. J. Chem. Soc., Perkin Trans. 1 1996, 2561.
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43
-
-
77951693412
-
-
Unlike aryl azides, the (electron-rich) five-membered heteroaryl counterparts are usually hardly available from corresponding amines via diazonium salts
-
(a) Unlike aryl azides, the (electron-rich) five-membered heteroaryl counterparts are usually hardly available from corresponding amines via diazonium salts,
-
-
-
-
44
-
-
0001638002
-
-
(b) For the first report of azido-group-transfer reaction with thiophenes andbenzothiophenes, see: Spagnolo, P.; Zanirato, P. J. Org. Chem. 1978, 43, 3539.
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Spagnolo, P.1
Zanirato, P.2
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45
-
-
0039240285
-
-
For original general information on the synthesis of five-membered heteroaromatic azides, see
-
(c) For original general information on the synthesis of five-membered heteroaromatic azides, see: Funicello, M.; Spagnolo, P.; Zanirato, P. Acta Chem. Scand. 1993, 47, 231.
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Acta Chem. Scand.
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Funicello, M.1
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Zanirato, P.3
-
46
-
-
77951673995
-
-
note
-
4 and finally evaporated in vacuo. Column chromatography of the crude on a Florisil column using PE as eluant isolated the title azide (0.71 mmol, 66%) as yellow thick oil. Physical and IR and NMR spectral data were fully consistent with those originally reported.
-
-
-
-
47
-
-
77951687874
-
-
note
-
3): S = 132.78,132.71, 132.59, 132.51, 131.99, 131.75, 128.77, 128.67, 128.53, 128.44, 123.57, 121.18, 120.05, 119.84, 110.88, 110.67.
-
-
-
-
48
-
-
77951686869
-
-
note
-
13C NMR, and MS spectral data.
-
-
-
-
49
-
-
77951684509
-
-
Reactions of enones with (benzothien-3-yl)iminophosphoranes bearing methyl substituent(s) on phosphorus were shown to form b-fused pyridines due to aza-Wittig electrocyclization along with those due to opposite regiochemistry, see ref. 10b,c.
-
Reactions of enones with (benzothien-3-yl)iminophosphoranes bearing methyl substituent(s) on phosphorus were shown to form b-fused pyridines due to aza-Wittig electrocyclization along with those due to opposite regiochemistry, see ref. 10b,c.
-
-
-
-
50
-
-
77951675884
-
-
Replacement of phenyl with electron-donating methyl group(s) on phosphorus could enhance the reactivity of previous (benzothien-2-yl)- and, especially, (benzothien-3yl)imino-phosphoranes with enones, see ref. 10b,c.
-
Replacement of phenyl with electron-donating methyl group(s) on phosphorus could enhance the reactivity of previous (benzothien-2-yl)- and, especially, (benzothien-3yl)imino-phosphoranes with enones, see ref. 10b,c.
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-
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