A simple method for iodination of heterocyclic compounds
623
3
,5-Diiodo-2-methylpyridine (C H I N)
6
12. Benhida R, Blanchard P, Fourrey J-L (1998) Tetrahedron Lett
39:6849
5 2
1
Yellow powder; yield 48%; m.p.: 138–140 °C; H NMR
500 MHz, CDCl ): d = 2.71 (s, 3H, Me), 7.59 (d, 1H,
JHH = 3.5 Hz, H-4), 8.39 (d, 1H, J = 3.5 Hz, H-6)
1
3. Maegawa Y, Goto Y, Inagaki S, Shimada T (2006) Tetrahedron
Lett 47:6957
(
4
3
4
HH
14. Kim MM, Ruck RT, Zhao D, Huffman MA (2008) Tetrahedron
Lett 49:4026 (and references cited therein)
1
3
ppm; C NMR (125 MHz, CDCl ): d = 25.2 (Me), 122.8
3
1
1
1
5. Laroche C, Kerwin SM (2009) Tetrahedron Lett 50:5194
6. Siskovic DR, Roth BD, Wilson MW (1990) J Med Chem 33:31
7. Lavecchia G, Berteina-Raboin S, Guillaumet G (2004) Tetrahe-
dron Lett 45:6633
(
C-3), 124.2 (C-5), 136.8 (C-4), 148.1 (C-6), 155.6 (C-2)
ppm.
4
-Ethoxy-3,5-diiodopyridine (C H I NO)
7 7 2
1
8. Maloney KM, Nwakpuda E, Kuethe JT, Yin J (2009) J Org Chem
7
1
Yellow powder; yield 75%; m.p.: 165–167 °C; H NMR
4:5111
3
(
500 MHz, MeOH-d ): d = 1.19 (t, 3H, J = 7.2 Hz,
19. Kondo Y, Shilai M, Uchiyama M, Sakamoto T (1999) J Am
Chem Soc 121:3539
20. Schlosser M, Bobbio C, Rausis T (2005) J Org Chem 70:2494
4
HH
3
Me), 3.61 (q, 2H, J = 7.2 Hz, OCH ), 8.31 (s, 2H)
HH
2
1
3
ppm; C NMR (125 MHz, MeOH-d ): d = 18.4 (Me),
5
4
2
1. Waldo JP, Mehta S, Larock RC (2008) J Org Chem 73:6666
8.3 (OCH ), 128.3 (2 C), 147.5 (2 CH), 163.1 (C) ppm.
2
22. For a recent review see: Stavber S, Jereb M, Zupan M (2008)
Synthesis 1487
2
2
3. Khalilzadeh MA, Hosseini A, Shokrollahzadeh M, Halvagar MR,
Ahmadi D, Mohannazadeh F, Tajbakhsh M (2006) Tetrahedron
Lett 47:3525
4. Krassowska-Swiebocka B, Prokopienko G, Skulski L (2005)
Molecules 10:394
5. Luli n´ ski P, Sosnowski M, Skulski L (2005) Molecules 10:516
6. Miyaura N, Suzuki A (1995) Chem Rev 95:2457
7. Negishi A (1982) Acc Chem Res 15:340
8. Buchwald SL (2002) Top Curr Chem 219:131
9. Rodewald Z, Plszek E (1937) Ber 70:1159
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