Highly efficient one- or two-step sequences for the synthesis of fine chemicals from versatile nitroalkanes

Tetrahedron

Volumn 63, Issue 49, 2007, Pages 12099-12121

  Ballini, Roberto ^a   Palmieri, Alessandro ^a   Righi, Paolo ^b  

^a Università and Consorzio Interuniversitario 'La Chimica per l'Ambiente' INCA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Eco friendly; Fine chemicals; Green chemistry; Nitroalkanes; One pot synthesis

Indexed keywords

1,3 DINITROPROPANE DERIVATIVE; 1,3 DIOL DERIVATIVE; 1,4 DIKETONE DERIVATIVE; 1,4 DIOL DERIVATIVE; 3,5 ALKYLACETOPHENONE DERIVATIVE; 4 HYDROXY 4,5 DIHYDROISOXAZOLE DERIVATIVE; ACETAL DERIVATIVE; ALDEHYDE DERIVATIVE; ALKANOL; ALPHA,OMEGA DICARBONYL DERIVATIVE; ALPHA,OMEGA DICARBOXYLIC ACID DIMETHYL ESTER; AROMATIC COMPOUND; BENZENE 1,2,3,5 TETRACARBOXYLIC ACID DERIVATIVE; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXANE DERIVATIVE; CYCLOPENTONE DERIVATIVE; DELTA NITROALKANOL DERIVATIVE; DIHYDROPYRANOL DERIVATIVE; ESTER DERIVATIVE; GAMMA KETO ESTER DERIVATIVE; GAMMA OXOALDEHYDE DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROXYTETRAHYDROFURAN DERIVATIVE; ISOXAZOLE DERIVATIVE; KETONE DERIVATIVE; METHYLBENZOIC ACID DERIVATIVE; NITRILE; NITROALKANE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

BIOLOGICAL ACTIVITY; CHEMICAL BOND; CHEMICAL STRUCTURE; ELIMINATION REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE; ONE POT SYNTHESIS; OXIDATION; PRIORITY JOURNAL; PROTON TRANSPORT; REDUCTION; REVIEW; STEREOCHEMISTRY;

EID: 35448961213     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.024     Document Type: Review

References (197)

1. Sheldon R.A. CHEMTECH (March 1994) 38
2. Poliakoff M., Fitzpatrick J.M., Farren T.R., and Anastas P.T. Science 297 (2002) 807
3. Hall N. Science 266 (1994) 32
4. Rosini G., and Ballini R. Synthesis (1988) 833
5. In: Feuer H., and Nielsen A.T. (Eds). Nitro Compounds: Recent Advances in Synthesis and Chemistry (1990), VCH, Weinheim
6. Ono N. The Nitro Group in Organic Synthesis (2001), Wiley-VCH, New York, NY
7. In: Patai S. (Ed). The Chemistry of Amino, Nitroso, Nitro and Related Groups (1996), Wiley, Chichester, UK
8. Adams J.P. J. Chem. Soc., Perkin Trans. 1 (2002) 2586
9. Ballini R., and Rinaldi A. Tetrahedron Lett. 35 (1994) 9247
10. Rosini G., Ballini R., and Zanotti V. Synthesis (1983) 137
11. Ballini R., and Petrini M. Tetrahedron 60 (2004) 1017
12. Seebach D., Colvin E.W., Lehr F., and Weller T. Chimia 33 (1979) 1
13. Corey E.J., and Cheng X.-M. The Logic of Chemical Synthesis (1989), John Wiley and Sons, New York, NY
14. Linberg T. Strategies and Tactics in Organic Synthesis (1989), John Wiley and Sons, New York, NY
15. Ho T.L. Tactics of Organic Synthesis Vol. 1 (1994), Academic, San Diego, UK
16. Feldman K.S. Synlett (1995) 217
17. Schapoehler S., Scheper T., Schuegerl K., and Barenschee E.R. Front. Bioprocess. 2, Proc. (1990) 50
18. Chem. Abstr. 117 (1992) 111298
19. Harada T., Wada I., Wada I., and Oku A. Tetrahedron Lett. 28 (1987) 4181
20. Patai S. The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulphur Analogues (1980), Interscience, New York, NY Part 2, p 721
21. Rieger M. Cosmet. Toiletries 107 (1992) 85
22. Majewski M., Gleave D.M., and Nowak P. Can. J. Chem. 73 (1995) 1616
23. Darabantu M., Mager S., Plé G., and Puscas C. Heterocycles 41 (1995) 2327
24. Didier, S.; Michel, P. Eur. Pat. Appl. EP 714,882, 1996;
25. Chem. Abstr. 125 (1996) 114385
26. Ballini R., Barboni L., and Pintucci L. Synlett (1997) 1389
27. Stach H., and Hesse M. Tetrahedron 44 (1988) 1573
28. Patai S. The Chemistry of Carboxylic Acids and Esters (1969), Interscience, New York, NY
29. Cabrera Escribano F., Alcántara M.P., and Gómez-Sánchez A. Tetrahedron Lett. 29 (1988) 6001
30. Pham-Huu D.-P., Petruošvá M., BeMiller J.N., and Petruš L. Tetrahedron Lett. 40 (1999) 3053
31. Axenrod T., Watnick C., and Yazdekhasti H. J. Org. Chem. 60 (1995) 1959
32. Marchand M.P., Rajagopal D., and Bott S.G. J. Org. Chem. 60 (1995) 4993
33. Wade P.A., Dailey W.P., and Carrol P.J. J. Am. Chem. Soc. 109 (1987) 5452
34. Xiao H.-M., Fan J.-F., Gu Z.-M., and Dong H.-Z. Chem. Phys. 226 (1998) 15
35. Derri Alcántara M.-P., Cabrera Escribano F., Gómez-Sánchez A., Diánez M., Estrada M.D., López-Castro A., and Pérez-Garrido S. Synthesis (1996) 64
36. Barrett A.G.W., and Graboski G.G. Chem. Rev. 86 (1986) 751
37. Perekalin V.V., Lipina E.S., Berestovitskaya V.M., and Efremov D.A. Nitroalkenes: Conjugated Nitro Compounds (1994), John Wiley, Chichester, UK
38. Rosini G., Ballini R., Petrini M., and Sorrenti P. Synthesis (1985) 515
39. Rosini G., Marotta E., Ballini R., and Petrini M. Synthesis (1986) 237
40. Ballini R., Castagnani R., and Petrini M. J. Org. Chem. 57 (1992) 2160
41. Ballini R., Bosica G., Fiorini D., and Palmieri A. Synthesis (2004) 1938
42. Ho T.-L. Polarity Control for Synthesis (1991), Wiley, New York, NY Chapter 7
43. Bean G.P. In: Jones R.A. (Ed). The Chemistry of Heterocyclic Compounds: Pyrroles (1990), Wiley, New York 206-216
44. Ho H.-L. Synth. Commun. 4 (1974) 265
45. Eleison R.A. Synthesis (1973) 397
46. Piancatelli G., D'Auria M., and D'Onofrio F. Synthesis (1994) 867
47. Miyakoshi T. Org. Prep. Proced. Int. 21 (1989) 659
48. See for example:
49. Cardellach J., Font J., and Ortuno R.M.J. Heterocycl. Chem. 21 (1984) 327
50. Short K.M., and Mjalli M.M.A. Tetrahedron Lett. 38 (1997) 359
51. Frenette R., Monette M., Bernstein M.A., Young R.N., and Verhoeven T.R. J. Org. Chem. 56 (1991) 3083
52. Ohkuma T., Kitamura M., and Noyori R. Tetrahedron Lett. 31 (1990) 5509
53. Ballini R., Bosica G., and Gigli F. Tetrahedron 54 (1998) 7573
54. Ballini R., Bosica G., Fiorini D., and Petrini M. Tetrahedron Lett. 43 (2002) 5233
55. Ballini R., Barboni L., Bosica G., and Fiorini D. Synthesis (2002) 2725
56. Ballini R., Fiorini D., Gil M.V., Palmieri A., Román E., and Serrano J.A. Tetrahedron Lett. 44 (2003) 2795
57. Occhiato E.G., Guarna A., De Sarlo F., and Scarpi D. Tetrahedron: Asymmetry 6 (1995) 2971
58. Yoda H., Mizutani M., and Takabe K. Heterocycles 48 (1998) 679
59. Hajois Z.G., Wachter M.P., Werblood H.M., and Adams R.E. J. Org. Chem. 49 (1984) 2600
60. Lee J.Y., and Kim B.H. Tetrahedron 52 (1996) 571
61. Gonser P., Jakupovic J., and Mungal G.M. Phytochemistry 30 (1991) 899
62. In: Katrinsky A.R., Meth-Cohn O., and Rees C.V. (Eds). Comprehensive Organic Functional Group Transformations Vol. 6 (1995), Pergamon, Oxford
63. Ballini R., Barboni L., and Giarlo G. J. Org. Chem. 68 (2003) 9173
64. Picher M.T., Tortajada A., and Seoane E. An. Quim., Ser. C 79 (1983) 404
65. Chem. Abstr. 102 (1985) 21228
66. Ogener G. Acta Chem. Scand. 27 (1973) 1601
67. Gerson H., and Shanks L. Can. J. Microbiol. 22 (1976) 1198
68. Chem. Abstr. 85 (1976) 117344
69. See for example:
70. Deodhar V.B., Dalavoy V.S., and Nayak U.R. Indian J. Chem., Sect. B 17 (1979) 375
71. Ashkenazi P., Kattering J., Migdal S., Gutman A.L., and Ginsburg D. Helv. Chim. Acta 68 (1985) 2033
72. Hass, P.; Hettel, H. Ger. Offen. DE 3,124,855, 1983;
73. Chem. Abstr. 98 (1983) 180393
74. Kajii, Y. Japan, 71 06, 106, 1971;
75. Chem. Abstr. 76 (1972) 4816
76. Von Praun, F.; Amende, J. Ger. Offen. 2,143,010, 1973;
77. Chem. Abstr. 78 (1973) 126134
78. Feuer H., and Pivawer P.M. J. Org. Chem. 34 (1969) 2917
79. Ballini R., and Bosica G. Tetrahedron 53 (1997) 16131
80. Ballini R., Curini M., Epifano F., Marcotullio M.C., and Rosati O. Synlett (1998) 1149
81. Barco A., Benetti S., Baraldi P.G., and Simoni D. Synthesis (1981) 199
82. Bestman H.J., Koschatzky K.H., Stransky W., and Vostrowsky O. Tetrahedron Lett. 17 (1976) 353
83. Muchowski J.M., and Venuti M.C. J. Org. Chem. 46 (1981) 459
84. Stowell J.C., and King B.T. Synthesis (1983) 2178
85. Ballini R., Petrini M., and Polzonetti V. Synthesis (1992) 355
86. Patai S., and Rappoport Z. The Chemistry of Enones (1989), John Wiley and Sons, Chichester, UK Parts 1 and 2
87. Lee V.J. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon, Oxford 69
88. Ap Simon J. The Total Synthesis of Natural Products (1988), John Wiley and Sons, New York, NY
89. Hwu J.R., Hakimelahi G.H., and Chou C.T. Tetrahedron Lett. 33 (1992) 6469 and references cited therein
90. Galatis P., and Parks D.J. Tetrahedron Lett. 35 (1994) 6611
91. Perlmutter P. Conjugate Addition Reactions in Organic Synthesis (1992), Pergamon, Oxford
92. See Ref. 8;
93. Ballini R., and Bosica G. Tetrahedron 51 (1995) 4213
94. Fleming F.F., and Wang Q. Chem. Rev. 103 (2003) 2035
95. Ballini R., Fiorini D., Gil M.V., and Palmieri A. Tetrahedron Lett. 44 (2003) 9033
96. Cromie L., Edgar A.J.B., Harper S.H., Lowe M.H., and Thompson D. J. Chem. Soc. (1950) 3552
97. Welch S.C., Assereg J.H., and Glase S.A. J. Org. Chem. 52 (1987) 1440
98. Le Mahieu R.A., Tabenkin B., Berger J., and Kierstead R.W. J. Org. Chem. 35 (1970) 1687
99. Piers E., Cheng K.F., and Nagakura I. Can. J. Chem. 60 (1982) 1256
100. Ballini R. Synthesis (1993) 687
101. Sugahara T., and Ogasawara K. Synlett (1999) 419
102. Dols P.P.M.A., Klunder A.J.H., and Zwanenburg B. Tetrahedron 50 (1994) 8515
103. Ballini R., Bosica G., Fiorini D., Gil M.V., and Petrini M. Org. Lett. 3 (2001) 1265
104. Ballini R., Barboni L., Bosica G., Filippone P., and Peretti S. Tetrahedron 56 (2000) 4095
105. Ballini R., Barboni L., Fiorini D., Giarlo G., and Palmieri A. Green Chem. 7 (2005) 828
106. Eicher T., and Hauptmann S. The Chemistry of Heterocycles (1995), Thieme, Stuttgart
107. Boivin T.L.B. Tetrahedron 43 (1987) 3309
108. Harding K.E., and Tiner T.H. Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon, Oxford p663
109. See Ref. 29a.
110. See for example:
111. Westley J.W. Polyether Antibiotics (1982), Marcel Dekker, New York, NY
112. Barlett P.A. In: Morrison J.D. (Ed). Asymmetric Synthesis Vol. 3 (1984), Academic, New York, NY
113. Ballini R., Barboni L., Fiorini D., and Palmieri A. Synlett (2004) 2618
114. Perron F., and Albizati K.F. Chem. Rev. 89 (1989) 1617
115. Ballini R., Petrini M., and Rosini G. Tetrahedron 46 (1990) 7531
116. Franche W., Hindorf G., and Reith W. Angew. Chem., Int. Ed. Engl. 17 (1978) 862
117. Baker R., Herbert R., Howse P.E., Jones O.T., Francke W., and Reith W. J. Chem. Soc., Chem. Commun. (1980) 52
118. Gariboldi P., Verotta L., and Fanelli R. Experientia (1983) 853
119. Francke W., Reith W., Bergstrom G., and Tengo J. Z. Naturforsch., C: Biosci. 36 (1981) 928
120. Mori K., and Katsurada M. Liebigs Ann. Chem. (1984) 157
121. Ballini R., and Petrini M. J. Chem. Soc., Perkin Trans 1 (1992) 3159
122. Padwa A. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon, Oxford 1069
123. For examples, see:
124. Vogel P., and Schaller C. Synlett (1999) 1219
125. Schaller C., Vogel P., and Jäger V. Carbohydr. Res. 314 (1998) 25
126. Wade P.A., Shah S.S., and Govindarajan L. J. Org. Chem. 59 (1994) 7199
127. Panek J.S., and Beresis R.T. J. Am. Chem. Soc. 115 (1993) 7898
128. Yin H., Franck R.W., Chen S.-L., Quigley G.J., and Todaro L. J. Org. Chem. 57 (1992) 644
129. Jäger V., and Schröter D. Synthesis (1990) 556
130. Schwab W., and Jäger V. Angew. Chem., Int. Ed. Engl. 20 (1981) 603
131. It has also been found that a 4-oxygenated-4,5-dihydroisoxazole derivative is itself biologically active as a galactosidase inhibitor. Schaller C., Demange R., Picasso S., and Vogel P. Bioorg. Med. Chem. Lett. (1999) 277
132. 68b,e
133. Davis F.A., Kumar A., Reddy R.E., Chen B.-C., Wade P.A., and Shah S.W. J. Org. Chem. 58 (1993) 7591
134. Zhang A., Kan Y., Zhao G.-L., and Jiang B. Tetrahedron 56 (2000) 965
135. Wallace R.H., Liu J., Zong K.K., and Eddings A. Tetrahedron Lett. 38 (1997) 6791
136. Liu J., Eddings A., and Wallace R.H. Tetrahedron Lett. 38 (1997) 6795
137. Rosini G. The Henry (Nitroaldol) Reaction. In: Trost B.M., and Heathcock C.H. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, Oxford 321 and references cited therein
138. Rosini G., Galarini R., Marotta E., and Righi P. J. Org. Chem. 55 (1990) 781
139. Rosini G., Marotta E., Righi P., and Seerden J.-P. J. Org. Chem. 56 (1991) 6258
140. Galli C., Marotta E., Righi P., and Rosini G. J. Org. Chem. 60 (1995) 6624-6626
141. Marotta E., Baravelli M., Maini L., Righi P., and Rosini G. J. Org. Chem. 63 (1998) 8235
142. Le Merrer Y., Dureault A., Greck C., Micos-Lauguin D., Gravier G., and Depazay J.C. Heterocycles 25 (1987) 541
143. Piancatelli G., Margherita R., De Mico A., Parlanti L., and Vescovi A. J. Org. Chem. 62 (1997) 6974
144. Marotta E., Micheloni L.M., Scardovi N., and Righi P. Org. Lett. 3 (2001) 727
145. Righi P., Scardovi N., Marotta E., ten Holte P., and Zwanenburg B. Org. Lett. 4 (2002) 497
146. Righi P., Marotta E., Landuzzi A., and Rosini G. J. Am. Chem. Soc. 118 (1996) 9446
147. For the use of the temporary silicon connection in organic synthesis see:. Stork G., and Kim G. J. Am. Chem. Soc. 114 (1992) 1087
148. For a review see:. Bols M., and Skydstrup T. Chem. Rev. 95 (1995) 1253
149. Marotta E., Righi P., and Rosini G. Tetrahedron Lett. 39 (1998) 1041
150. This value was calculated following:. Bertz S.H., and Sommer T.J. Applications of Graph Theory to Synthesis Planning: Complexity, Reflexivity, and Vulnerability. In: Hudlicky T. (Ed). Organic Synthesis: Theory and Applications Vol. 2 (1993), JAI, Greenwich, CT 67 For a comparison, consider that a Diels-Alder reaction, one of the most complexity increasing reactions known, normally gives values around 100
151. For a review, see:. Kislyi V.V., Samet A.V., and Semenov V.V. Curr. Org. Chem. 5 (2001) 553
152. Alvarez-Ibarra C., Csákÿ A.G., and Gómez de la Oliva C. J. Org. Chem. 65 (2000) 3544
153. Tsukamoto T., Kitazume T., McGuire J.J., and Coward J.K. J. Med. Chem. 39 (1996) 66
154. Hollinshead S.P., Trudell M.L., Skolnick P., and Cook J.M. J. Med. Chem. 33 (1990) 1062
155. Shipchandler M.T. Synthesis (1979) 666
156. 86
157. Kornblum N., Chalmers M.E., and Daniels R. J. Am. Chem. Soc. 77 (1955) 6654
158. Kornblum N., Blackwood R.K., and Powers J.W. J. Am. Chem. Soc. 79 (1957) 2507
159. Kornblum N., and Eicher J.H. J. Am. Chem. Soc. 78 (1956) 1494
160. Gelbard G., and Colonna S. Synthesis (1977) 113
161. The use of tetralkylammonium nitrites has also been reported:. Munz R., and Simchen G. Liebigs Ann. Chem. (1979) 628
162. Scardovi N., Casalini A., Peri F., and Righi P. Org. Lett. 4 (2002) 965
163. 86
164. See Ref. 95.
165. La Rock R.C. Comprehensive Organic Transformations. 2nd ed. (1999), Wiley-VCH, New York, NY p 187
166. Zhang L., Nadzan A.M., Heyman R.A., Love D.L., Mais D.E., Croston G., Lamph W.W., and Boehm M.F. J. Med. Chem. 39 (1996) 2659
167. Steinbaugh B.A., Hamilton H.W., Vara Prasad J.V.N., Para K.S., Tummino P.J., Fergusson D., Lunney E.A., and Blankley C.J. Bioorg. Med. Chem. Lett. 6 (1996) 1099
168. Connolly C.J.C., Hamby J.M., Schroeder M.C., Barvian M., Lu G.H., Panek R.L., Amar A., Shen C., Kraker A.J., Fry D.W., Klohs W.D., and Doherty A.M. Bioorg. Med. Chem. Lett. 7 (1997) 2415
169. Zhang X., Pais G.C.G., Svarovskaia E.S., Marchand C., Johnson A.A., Karki R.G., Nicklaus M.C., Pathak V.K., Pommier Y., and Burke jr T.R. Bioorg. Med. Chem. Lett. 13 (2003) 1215
170. Li J.-H., Bigge C.F., Williamson R.M., Borovsky S.A., Vartanian M.G., and Ortwine D.F. J. Med. Chem. 38 (1995) 1955
171. Choi K., and Hamilton A.D. J. Am. Chem. Soc. 125 (2003) 10241
172. Felder T., and Schalley C.A. Angew. Chem., Int. Ed. 42 (2003) 2258
173. Ballini R., Barboni L., Fiorini D., Giarlo G., and Palmieri A. Chem. Commun. (2005) 2633
174. Boyle, F. T.; Davies, G. M.; Wardleworth, J. M.; Arnould, J. C.U.S. Patent 6,414,145, 2002;
175. Chem. Abstr. (1998) 527321
176. Cao R., Shi Q., Sun D.-F., Hong M.-C., Bi W., and Zhao Y. Inorg. Chem. 41 (2002) 6161
177. Shi Q., Cao R., Sun D.-F., Hong M.-C., and Liang Y.-C. Polyhedron 20 (2001) 3287
178. Li Y., Hao N., Lu Y., Wang E., Kang Z., and Hu C. Inorg. Chem. 42 (2003) 3119
179. Li Y., Zhang H., Wang E., Hao N., Hu C., Yan Y., and Hall D. New J. Chem. 26 (2002) 1619
180. Yavari I., Moradi L., and Mirzaei A. Helv. Chim. Acta 89 (2006) 2918
181. Rosini G., Ballini R., Sorrenti P., and Petrini M. Synthesis (1984) 607
182. Ballini R., Bosica G., and Parrini M. Tetrahedron Lett. 39 (1998) 7963
183. Ballini R., Bosica G., Fiorini D., and Palmieri A. Tetrahedron 61 (2005) 8971
184. Ballini R., Castagnani R., and Marcantoni E. J. Chem. Soc., Perkin Trans 1 (1992) 3161
185. Caglioti L., and Grasselli P. Chem. Ind. (London) (1964) 153
186. Caglioti L. Tetrahedron 22 (1966) 487
187. Caglioti L. Org. Synth. 52 (1972) 122
188. Roelofs W.L., and Cardé R.T. Science 171 (1971) 684
189. Krasnoff S.B., and Roelofs W.L. Nature 333 (1988) 263
190. Diaz N. Proc. Am. Soc. Hortic. Sci., Trop. Reg. 24 (1976) 115
191. Chem. Abstr. 91 (1979) 106770
192. Hameoda H., Nakai K., Nakagawa M., and Miyazawa M. Yukagaku 38 (1989) 689
193. Chem. Abstr. 112 (1990) 34639
194. Yasuhara A., and Fuwa K. Agric. Biol. Chem. 46 (1982) 1761
195. Jiang P., and Gao Z. Zhongguo Zhongyao Zazhi 15 (1990) 488
196. Chem. Abstr. 114 (1991) 3476
197. Ballini R., and Bosica G. J. Chem. Res., Synop. (1993) 371