Application of organic azides for the synthesis of nitrogen-containing molecules

Synlett

Volumn , Issue 1, 2012, Pages 21-44

  Chiba, Shunsuke ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

azides; nitrogen containing heterocycles; oxygenations; radical reactions; redox reactions

Indexed keywords

1,3 DICARBONYL COMPOUND; 2 AZIDOCYCLOBUTANOL; ALKYNE; ALPHA AZIDO CARBONYL COMPOUND; AZASPIROCYCLOHEXADIENONE; AZIDE; CARBON; CARBONYL DERIVATIVE; COPPER; CYCLIC 2 AZIDO ALCOHOL; CYCLOPROPANOL; ISOINDOLE DERIVATIVE; ISOQUINOLINE; ISOQUINOLINE DERIVATIVE; MANGANESE; NITROGEN; OXYGEN; PALLADIUM; PROPANOL; PYRROLE; RHODIUM; UNCLASSIFIED DRUG; VINYL AZIDE;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; DISSOCIATION; MOLECULE; NITROGEN CONTAINING MOLECULE; ONE POT SYNTHESIS; ORGANIC CHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; THERMAL STIMULATION;

EID: 84655176396     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290108     Document Type: Article

References (166)

1. Griess P, Proc. R. Soc. London 1864 13 375
2. Curtius T, Ber. Dtsch. Chem. Ges. 1890 23 3023
3. For reviews, see:, Lang S, Murphy J A., Chem. Soc. Rev. 2006 35 146
4. Bräse S, Gil C, Knepper K, Zimmermann V, Angew. Chem. Int. Ed. 2005 44 5188
5. Scriven E F. V., Turnbull K, Chem. Rev. 1988 88 297
6. Labbe G, Chem. Rev. 1969 69 345
7. Boyer J H., Canter F C., Chem. Rev. 1954 54 1
8. Smith P A. S., Org. React. 1946 3 337
9. For safety issues on the handling of organic azides, see:, Keicher T, Löbbecke S, In Organic Azides: Syntheses and Applications Bräse S Banert K John Wiley & Sons Chichester 2010 3
10. Medal M, Tornoe C W., Chem. Rev. 2008 108 2952
11. Schilling C, Jung N, Bräse S, In Organic Azides: Syntheses and Applications Bräse S Banert K John Wiley & Sons Chichester 2010 269
12. For reviews, see:, Katsuki T, Chem. Lett. 2005 34 1304
13. Driver T G., Org. Biomol. Chem. 2010 8 3831
14. Trost B M., Angew. Chem. Int. Ed. Engl. 1995 34 259
15. Trost B M., Science (Washington, DC, U.S.) 1991 254 1471
16. Wender P A., Verma V A., Paxton T J., Pillow T H., Acc. Chem. Res. 2008 41 40
17. Wender P A., Croatt M P., Witulski B, Tetrahedron 2006 62 7505
18. Timén Å S., Risberg E, Somfai P, Tetrahedron Lett. 2003 44 5339
19. Söderberg B C. G., Curr. Org. Chem. 2000 4 727
20. Knittel D, Synthesis 1985 186
21. For prior studies on iminyl radical formation from vinyl azides, see:, Montevecchi P C., Navacchia M L., Spagnolo P, J. Org. Chem. 1997 62 5864
22. Bamford A F., Cook M D., Roberts B P., Tetrahedron Lett. 1983 24 3779
23. For our previous report on rhodium(II)-catalyzed indole formation from 2-aryl-2 H -azirines, see:, Chiba S, Hattori G, Narasaka K, Chem. Lett. 2007 36 52
24. Alves M J., Gilchrist T L., Sousa J H., J. Chem. Soc., Perkin Trans. 1 1999 1305
25. Alves M J., Ferreira P M. T., Maia H L. S., Monteiro L S., Gilchrist T L., Tetrahedron Lett. 2000 41 4991
26. Carlson R M., Lee S Y., Tetrahedron Lett. 1969 10 4001
27. Leonard N J., Zwanenburg B, J. Am. Chem. Soc. 1967 89 4456
28. Law K W., Lai T F., Sammes M P., Katritzky A R., Mak T C. W., J. Chem. Soc., Perkin Trans. 1 1984 111
29. Laurent A, Mison P, Nafti A, Pellissier N, Tetrahedron 1979 35 2285
30. Padwa A, Kulkarni Y, Tetrahedron Lett. 1979 20 107
31. FariadosSantosFilho P, Schuchardt U, Angew. Chem. Int. Ed. Engl. 1977 16 647
32. Nair V, George T G., Tetrahedron Lett. 2000 41 3199
33. Gilchrist T L., Mendonça R, Synlett 2000 1843
34. Palacios F, Aparicio D, delosSantos J M., PerezdeHeredia I, Rubiales G, Org. Prep. Proced. Int. 1995 27 171
35. Chiba S, Wang Y.-F, Lapointe G, Narasaka K, Org. Lett. 2008 10 313
36. Ng E P. J., Wang Y, Hui B W.-Q, Lapointe G, Chiba S, Tetrahedron 2011 67 7728
37. Moody C J., In Comprehensive Organic Synthesis Vol. 7 Trost B M. Fleming I Ley S Pergamon Oxford 1991 21
38. Smolinsky G, Pryde C A., J. Org. Chem. 1968 33 2411
39. Labbé G, Angew. Chem. Int. Ed. Engl. 1975 14 775
40. Hemetsberger H, Knittle D, Weidmann H, Monatsh. Chem. 1970 101 161
41. MacKenzie A R., Moody C J., Rees C W., J. Chem. Soc., Chem. Commun. 1983 1372
42. Bolton R E., Moody C J., Pass M, Rees C W., Tojo G, J. Chem. Soc., Perkin Trans. 1 1988 2491
43. Iron(II)- and Rh(II)-catalyzed indole formation from azido-substituted cinnamates has been reported, see:, Bonnamour J, Bolm C, Org. Lett. 2011 13 2012
44. Stokes B J., Dong H, Leslie B E., Pumphrey A L., Driver T G., J. Am. Chem. Soc. 2007 129 7500
45. Ng E P. J., Wang Y.-F, Chiba S, Synlett. 2011 783
46. Wang Y.-F, Toh K K., Chiba S, Org. Lett. 2008 10 5019
47. For reviews on the synthesis of azaheterocycles using iminyl radicals, see:, Stella L, In Radicals in Organic Synthesis Vol. 2 Renaud P Sibi M P. Wiley-VCH Weinheim 2001 407
48. Zard S Z., Chem. Soc. Rev. 2008 37 1603
49. Kitamura M, Narasaka K, Bull. Chem. Soc. Jpn. 2008 81 539
50. Mikami T, Narasaka K, In Advances in Free Radical Chemistry Vol. 2 Zard S Z. JAI Stamford / CT 1999 45
51. Fallis A G., Brinza I M., Tetrahedron 1997 53 17543
52. Zard S Z., Synlett 1996 1148
53. For reviews, see:, Melikyan G G., Org. React. 1997 49 427
54. Snider B B., Chem. Rev. 1996 96 339
55. Alonso-Cruz C R., Kennedy A R., Rodríguez M S., Suárez E, Org. Lett. 2003 5 3729
56. Figgis B N., Raston C L., Sharma R P., White A H., Aust. J. Chem. 1978 31 2545
57. Fortner K C., Shair M D., J. Am. Chem. Soc. 2007 129 1032
58. Narasaka K, Miyoshi N, Iwakura K, Okauchi T, Chem. Lett. 1989 2169
59. Wang Y.-F, Toh K K., Ng E P. J., Chiba S, J. Am. Chem. Soc. 2011 133 6411
60. Wang Y.-F, Chiba S, J. Am. Chem. Soc. 2009 131 12570
61. 3, see:, Iwasawa N, Hayakawa S, Funahashi M, Isobe K, Narasaka K, Bull. Chem. Soc. Jpn. 1993 66 819
62. Iwasawa N, Hayakawa S, Isobe K, Narasaka K, Chem. Lett. 1991 1193
63. Chiba S, Cao Z Y., ElBialy S A. A., Narasaka K, Chem. Lett. 2006 35 18
64. Hasegawa E, Tsuchida H, Tamura M, Chem. Lett. 2005 34 688
65. Booker-Milburn K I., Jones J L., Sibley G E. M., Cox R, Meadows J, Org. Lett. 2003 5 1107
66. Booker-Milburn K I., Barker A, Brailsford W, Cox B, Mansley T E., Tetrahedron 1998 54 15321
67. Snider B B., Kwon T, J. Org. Chem. 1992 57 2399
68. For selected reports on the preparation of -lactams, see:, Zhou C.-Y, Che C.-M, J. Am. Chem. Soc. 2007 129 5828
69. Patil N T., Huo Z, Bajracharya G B., Yamamoto Y, J. Org. Chem. 2006 71 3612
70. Taylor P J. M., Bull S D., Andrews P C., Synlett 2006 1347
71. Hu T, Li C, Org. Lett. 2005 7 2035
72. The Renaud group has developed an elegant procedure for the synthesis of a series of -lactams and their derivatives by radical carboazidation of alkenes followed by the reduction of the azides and subsequent lactam formation, see:, Lapointe G, Schenk K, Renaud P, Chem. Eur. J. 2011 17 3207
73. Panchaud P, Ollivier C, Renaud P, Zigmantas S, J. Org. Chem. 2004 69 2755
74. Renaud P, Ollivier C, Panchaud P, Angew. Chem. Int. Ed. 2002 41 3460
75. Du H, Long J, Shi Y, Org. Lett. 2006 8 2827
76. For discussions on the racemization of cyclohexyl radicals, see:, Buckmelter A J., Kim A I., Rychnovsky S D., J. Am. Chem. Soc. 2000 122 9386
77. Roberts B P., Steel A J., J. Chem. Soc., Perkin Trans. 2 1992 2025; and references cited therein
78. For recent selected reports, see:, Thomas J B., Zhang L, Navarro H A., Carroll F I., J. Med. Chem. 2006 49 5597
79. Pluotno A, Carmeli S, Tetrahedron 2005 61 575
80. Kim I J., Dersch C M., Rothman R B., Jacobson A E., Rice K C., Bioorg. Med. Chem. 2004 12 4543
81. For a report on carbon-carbon bond formation at bridgehead iminium cations for preparing 1-alkylated 2-azabicyclo-[3.3.1]nonanes, see:, Yamazaki N, Suzuki H, Kibayashi C, J. Org. Chem. 1997 62 8280
82. Kraus G A., Hon Y.-S, Thomas P J., Laramay S, Liras S, Hanson J, Chem. Rev. 1989 89 1591
83. Bächli E, Vamvacas C, Schmid H, Karrer P, Helv. Chim. Acta 1957 40 1167
84. Borris R P., Guggisberg A, Hesse M, Helv. Chim. Acta 1984 67 455
85. Quirante J, Escolano C, Merino A, Bonjoch J, J. Org. Chem. 1998 63 968
86. Quirante J, Escolano C, Bosch J, Bonjoch J, J. Chem. Soc., Chem. Commun. 1995 2141
87. Brown H C., Yoon N M., J. Am. Chem. Soc. 1966 88 1464
88. Fujii T, Ohba M, Ohashi T, Tetrahedron 1993 49 1879
89. For recent reviews on carbon-hydrogen bond functionalization, see:, Colby D A., Bergman R G., Ellman J A., Chem. Rev. 2010 110 624
90. Lyons T W., Sanford M S., Chem. Rev. 2010 110 1147
91. Sun C.-L, Li B.-J, Shi Z.-J, Chem. Commun. 2010 46 677
92. Ackermann L, Vicente R, Kapdi A R., Angew. Chem. Int. Ed. 2009 48 9792
93. Chen X, Engle K M., Wang D.-H, Yu J.-Q, Angew. Chem. Int. Ed. 2009 48 5094
94. Kulkarni A A., Daugulis O, Synthesis 2009 4087
95. Kakiuchi F, Kochi T, Synthesis 2008 3013
96. Davies D L., Al-Duaij O, Fawcett J, Giardiello M, Hilton S T., Russell D R., Dalton Trans. 2003 4132
97. Ackermann L, Chem. Rev. 2011 111 1315
98. Li L, Brennessel W W., Jones W D., Organometallics 2009 28 3492
99. For reports on Rh(III)-catalyzed oxidative carbon-hydrogen bond functionalization/carbon-nitrogen bond formation with alkynes, see:, Stuart D R., Alsabeh P, Kuhn M, Fagnou K, J. Am. Chem. Soc. 2010 132 18326
100. Chen J, Song G, Pan C.-L, Li X, Org. Lett. 2010 12 5426
101. Su Y, Zhao M, Han K, Song G, Li X, Org. Lett. 2010 12 5462
102. Hyster T K., Rovis T, J. Am. Chem. Soc. 2010 132 10565
103. Rakshit S, Patureau F W., Glorius F, J. Am. Chem. Soc. 2010 132 9585
104. Morimoto K, Hirano K, Satoh T, Miura M, Org. Lett. 2010 12 2068
105. Mochida S, Umeda N, Hirano K, Satoh T, Miura M, Chem. Lett. 2010 39 744
106. Guimond N, Fagnou K, J. Am. Chem. Soc. 2009 131 12050
107. Fukutani T, Umeda N, Hirano K, Satoh T, Miura M, Chem. Commun. (Cambridge) 2009 5141
108. Stuart D R., Bertrand-Laperle M, Burgess K M. N., Fagnou K, J. Am. Chem. Soc. 2008 130 16474
109. For a report on the Rh(III)-catalyzed redox-neutral synthesis of azaheterocycles from benzhydroxamic acid derivatives and O -acetyloximes with alkynes, see:, Guimond N, Gouliaras C, Fagnou K, J. Am. Chem. Soc. 2010 132 6908
110. Too P C., Wang Y.-F, Chiba S, Org. Lett. 2010 12 5688
111. Wang Y.-F, Toh K K., Lee J.-Y, Chiba S, Angew. Chem. Int. Ed. 2011 50 5927
112. For reports on the use of DMF as a hydrogen radical source, see:, Kamiya I, Tsunoyama H, Tsukuda T, Sakurai H, Chem. Lett. 2007 36 646
113. Minisci F, Citterio A, Vismara E, Giordano C, Tetrahedron 1985 41 4157
114. Palla G, Tetrahedron 1981 37 2917
115. Auricchio S, Grassi S, Malpezzi L, Sartori A S., Truscello A M., Eur. J. Org. Chem. 2001 1183
116. Kim J, Chang S, J. Am. Chem. Soc. 2010 132 10272
117. Malkhasian A Y. S., Finch M E., Nikolovski B, Menon A, Kucera B E., Chavez F A., Inorg. Chem. 2007 46 2950
118. Teo J J., Chang Y, Zeng H C., Langmuir 2006 22 7369
119. Recent literature reports have shown that Cu(II)-TEMPO complexes work as ionic electrophiles, see:, Van Humbeck J F., Simonovich S P., Knowles R R., Macmillan D W. C., J. Am. Chem. Soc. 2010 132 10012
120. Michel C, Belanzoni P, Gamez P, Reedjik J, Baerends E J., Inorg. Chem. 2009 48 11909
121. Terao Y, Wakui H, Nomoto M, Satoh T, Miura M, Nomura M, J. Org. Chem. 2003 68 5236
122. Wakui H, Kawasaki S, Satoh T, Miura M, Nomura M, J. Am. Chem. Soc. 2004 126 8658
123. Nishimura T, Ohe K, Uemura S, J. Org. Chem. 2001 66 1455
124. Nishimura T, Uemura S, J. Am. Chem. Soc. 1999 121 11010
125. Nishimura T, Ohe K, Uemura S, J. Am. Chem. Soc. 1999 121 2645
126. Matsumura S, Maeda Y, Nishimura T, Uemura S, J. Am. Chem. Soc. 2003 125 8862
127. Nishimura T, Uemura S, J. Am. Chem. Soc. 2000 122 12049
128. Harayama H, Kuroki T, Kimura M, Tanaka S, Tamaru Y, Angew. Chem. Int. Ed. Engl. 1997 36 2352
129. Necas D, Tursky M, Kotora M, J. Am. Chem. Soc. 2004 126 10222
130. Terai H, Takaya H, Murahashi S.-I, Synlett 2004 2185
131. For a report on the Mn(III)-based -fission of cyclobutanol derivatives, see:, Snider B B., Vo N H., Foxman B M., J. Org. Chem. 1993 58 7228
132. Wang, Y.-F.; Toh, K. K.; Chiba, S. unpublished results.
133. Chiba S, Xu Y.-J, Wang Y.-F, J. Am. Chem. Soc. 2009 131 12886
134. Nitrile formation by radical fragmentation of 2-azido alcohols with cleavage of the carbon-carbon bond has been reported, see:, Hernández R, León E I., Moreno P, Suárez E, J. Org. Chem. 1997 62 8974
135. Shimizu I, Fujita M, Nakajima T, Sato T, Synlett 1997 887
136. Barz M, Herdweck E, Thiel W R., Angew. Chem. Int. Ed. 1998 37 2262
137. Cenini S, Gallo E, Caselli A, Ragaini F, Fantauzzi S, Piangiolino C, Coord. Chem. Rev. 2006 250 1234
138. Mi B.-X, Wang P.-F, Liu M.-W, Kwong H.-L, Wong N.-B, Lee C.-S, Lee S.-T, Chem. Mater. 2003 15 3148
139. Ding Y, Hay A S., J. Polym. Sci., Part A: Polym. Chem. 1999 37 3293
140. Gauvin S, Santerre F, Dodelet J P., Ding Y, Hlil A R., Hay A S., Anderson J, Armstrong N R., Gorjanc T C., DIorio M, Thin Solid Films 1999 353 218
141. Matuszewski B K., Givens R S., Srinivasachar K, Carlson R G., Higuchi T, Anal. Chem. 1987 59 1102
142. Zweig A, Metzler G, Maurer A, Roberts B G., J. Am. Chem. Soc. 1967 89 4091
143. Duan S, Sinha-Mahapatra D K., Herndon J W., Org. Lett. 2008 10 1541
144. Chen Y.-L, Lee M.-H, Wong W.-Y, Lee A W. M., Synlett 2006 2510
145. Chen Z, Müller P, Swager T M., Org. Lett. 2006 8 273
146. LeHoullier C S., Gribble G W., J. Org. Chem. 1983 48 2364
147. For reviews, see:, Nair V, Suja T D., Tetrahedron 2007 63 12247
148. Padwa A, In 1,3-Dipolar Cycloaddition Chemistry Vol. 2 Padwa A Wiley-Interscience New York 1984 316
149. Hui B W.-Q, Chiba S, Org. Lett. 2009 11 729
150. For the generation of imines from -azido ketones and esters under strong basic conditions, see:, Manis P A., Rathke M W., J. Org. Chem. 1980 45 4952
151. Edwards O E., Purushothaman K K., Can. J. Chem. 1964 42 712
152. For recent examples of the 6-electrocyclization of azatrienes, see:, Manning J R., Davies H M. L., J. Am. Chem. Soc. 2008 130 8602
153. Liu S, Liebeskind L S., J. Am. Chem. Soc. 2008 130 6918
154. Colby D A., Bergman R G., Ellman J A., J. Am. Chem. Soc. 2008 130 3645
155. Meketa M L., Weinreb S M., Nakao Y, Fusetani N, J. Org. Chem. 2007 72 4892
156. Tanaka K, Mori H, Yamamoto M, Katsumura S, J. Org. Chem. 2001 66 3099; and references cited therein
157. Chiba S, Zhang L, Ang G Y., Hui B W.-Q, Org. Lett. 2010 12 2052
158. Zhang L, Ang G.-Y, Chiba S, Org. Lett. 2010 12 3682
159. For the chemical reactivity of (acylperoxy)metals, see:, Cornell C N., Sigman M S., In Activation of Small Molecules Tolman W B. Wiley Weinheim 2006 159-186; and references cited therein
160. Chiba S, Zhang L, Lee J.-Y, J. Am. Chem. Soc. 2010 132 7266
161. For reviews, see:, Dohi T, Kita Y, Chem. Commun. (Cambridge) 2009 2073
162. Quideau S, Pouysegu L, Deffieux D, Synlett 2008 467
163. Ciufolini M A., Braun N A., Canesi S, Ousmer M, Chang J, Chai D, Synthesis 2007 3759
164. Kusama H, Yamashita Y, Uchiyama K, Narasaka K, Bull. Chem. Soc. Jpn. 1997 70 965
165. For GlyT1 transporter inhibitors bearing diazaspiro structures, see:, Marshall H R., WO 2008092879 2008, Dean A W., Porter R A., WO 2007014762 2007
166. Lucas H R., Li L, NarducciSarjeant A A., Vance M A., Solomon E I., Karlin K D., J. Am. Chem. Soc. 2009 131 3230