- Email: [email protected]
Synthesis of 2-selenoxo DHPMs by Biginelli reaction with Hf(OTf)4 as catalyst
Tetrahedron Letters 59 (2018) 987–990
Contents lists available at ScienceDirect
Tetrahedron Letters journal homepage: www.elsevier.com/locate/tetlet
Synthesis of 2-selenoxo DHPMs by Biginelli reaction with Hf(OTf)4 as catalyst Peiran Chen a,b,⇑, Mengdi Tu a a b
Donghua University, 2999 Renmin Road North, Songjiang District, Shanghai 201620, China Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032, China
a r t i c l e
i n f o
a b s t r a c t
Article history: Received 24 November 2017 Revised 22 January 2018 Accepted 23 January 2018 Available online 31 January 2018
By using Hf(OTf)4 as catalyst, a series of 2-selenoxo DHPMs have been synthesized efficiently in good yields by Biginelli reaction with selenourea as starting material. Ó 2018 Elsevier Ltd. All rights reserved.
Keywords: Hf(OTf)4 Selenourea 2-Selenoxo DHPMs Biginelli reaction
Since found in 1818, selenium was known as poison for a long time because of the health problems that it might lead to -such as livestock disease and intoxication.1 After in-depth study on its biological and pharmaceutical activities in the passing decades, selenium is now considered as an essential micronutrient element for mammals.2 More and more researches have been carried out on the preparation and bio-activities of seleno-containing compounds. For example, since its Sec-residue showed unique redox character, which might owe to the relative low redox potential of the selenium, selenocysteine was referred to as the 21st amino acid.3 A series of Se-containing compounds, such as ebselen and its derivatives, were synthesized as glutathione peroxidase (GPX) mimics and showed various bioactivities including anti-inflammatory, antiatherosclerotic, cytoprotective and antioxidative properties.4
H2N
O SeH COOH
L-Selenocysteine
N Ph Se ebselen
⇑ Corresponding author at: Donghua University, 2999 Renmin Road North, Songjiang District, Shanghai 201620, China. E-mail address: [email protected] (P. Chen). https://doi.org/10.1016/j.tetlet.2018.01.070 0040-4039/Ó 2018 Elsevier Ltd. All rights reserved.
3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) and their derivatives – which present in wide ranging natural products such as marine alkaloids5 – have attracted more and more attention since their broad spectrum of pharmacological activities such as antiviral, antitumour, antibacterial, antimalarial, antitubercular, antidiabetic, antiepileptic, antiproliferative activities, etc.6 As one of the most important multicomponent reactions (MCRs), Biginelli reaction provides an easy and effective process to prepare DHPMs (Scheme 1).7 Till now, the investigation of DHPMs, whether on preparation or on bio-activities, were focused on 2-oxo or 2-thioxo DHPMs. So far, the synthesis of 2-selenoxo DHPMs was rarely mentioned.8 As reported, the acid catalyst played a key role in the first step of Biginelli reaction to promotion the combination of aromatic aldehydes with urea.7i A wide range of Lewis acid catalysts such as SmI2,9 LaCl37H2O,10 CuSO45H2O,11 ZnCl2,12 ZnI2,13 CuI,14 GaI3,15 GaBr3/GaCl3,16 LiBr,17 InBr3,18 CdCl2,19 CeCl37H2O,20 FeCl36H2O/NiCl26H2O/HCl,21 NiFe2O4,22 GaCl323 have been reported to be used in Biginelli reaction for the preparation of 2-oxo or 2thio DHPMs. Recently, as an efficient Lewis acid catalyst, Hf(OTf)4 has been used to promote Friedel-Crafts reaction,24 Fries rearrangement,25 thioacetalization reaction26 and Ferrier rearrangement.27 Herein, we report our research for the preparation of 2-selenoxo-DHPMs by Biginelli reaction with Hf(OTf)4 as an efficient Lewis acid catalyst. First of all, we compared a series of the rare earth motel triflate for the catalytic efficiency. Reaction condition optimization was
988
P. Chen, M. Tu / Tetrahedron Letters 59 (2018) 987–990
O
O
O/S OR
+ ArCHO +
H2 N
O acid condition
Ar NH
O
NH2
N H
O/S
Scheme 1.
Table 1 Comparation of several Lewis acid catalysts in the Biginelli reaction using selenourea as starting material.a
Table 2 Preparation of 2-selenoxo DHPMs with Biginelli reaction promoted by Hf(OTf)4.a
O O
O O H3C
O
Se
+ PhCHO + OEt
catalyst
H2N
NH2
NH
O
120oC
N H
H3C
O
Se
+ ArCHO + H2N
OEt
NH2
Hf(OTf)4
Ar NH
O
120oC
N H
Se
Se
Entry
Catalyst
Reaction time
Conversion (%)b
1 2 3 4 5
In(OTf)3 Y(OTf)3 Hf(OTf)4 Yb(OTf)3 Sm(OTf)3
24 h 24 h 1h 24 h 24 h
Trace Trace 78 Trace Trace
a Reaction conditions: Ethyl acetoacetate(3mL) benzaldehyde (80 mg, 0.75 mmol), selenourea (61 mg, 0,75 mmol), cat. (5 mol%), 120 °C. b Isolated yield.
performed. Among In(OTf)3, Y(OTf)3, Sm(OTf)3, Hf(OTf)4 and Yb (OTf)3 we found Hf(OTf)4 was the most efficient (Table 1). With Hf(OTf)4 as the catalyst, a series of 2-selenoxo-DHPMs was performed with b-ketoester, selenourea, and various aryl aldehydes. Results of reaction were shown in Table 2. In our reaction system, a series of 2-selenoxo-DHPMs could be afforded in good yields. Selenourea showed relatively low reactive activity in Biginelli reaction, therefore higher reaction temperature (120 °C) was necessary. The aromatic aldehydes with electron-donating group (Table 2, entries 2–5) gave the corresponding DHPMs in higher yields than those with electron-withdrawing group at the same position (Table 2, entries 6, 7, 9–12). Moreover, naphthaldehyde and thiophenecarboxaldehyde also could afford the corresponding DHPMs effectively under the same conditions smoothly (Table 2, entries 14, 17, and 18), but the heteroatom on the aromatic ring of the aryl aldehyde might cause the decreasing of the yield. More b-dicarbonyl compounds, including methyl acetoacetate, t-butyl acetoacetate, benzyl acetoacetate, ethyl trifluoroacetoacetate, ethyl propionoacetoacetate and 2,4-pentanedione, have been tested as substrate in our Biginelli reaction system. But none of those b-dicarbonyl compounds afforded the required DHPMs. Ethyl trifluoroacetoacetate gave the by-product which might be formed in Knoevenagel route. No improvement could be achieved while the reaction temperature was elevated to 150 °C. Therefore, ethyl acetoacetate seems to be the best substrate for our reaction system. In summary, we have developed an efficient catalytic system for Biginelli reaction to synthesize 2-selenoxo DHPMs, which includes aryl aldehydes, ethyl acetoacetate, and selenourea as starting material and Hf(OTf)4 as the catalyst. Under our reaction conditions, corresponding 2-selenoxo DHPMs were afforded in moderate to excellent yields.
Entry ArCHO 1
CHO
Reaction Product time
Yield (%)b
1h
81
O NH
O N H
Se
2a 2
CHO
40 min
85
O
Me
Me NH
O N H
Se
2b CHO 40 min
3
73
OMe
MeO
O O
NH N H
Se
2c 4
CHO
10 min
OPh
94
O OPh
O
NH N H
Se
2d CHO 30 min
5
71
SMe
MeS
O NH
O N H
2e
Se
989
P. Chen, M. Tu / Tetrahedron Letters 59 (2018) 987–990 Table 2 (continued)
Table 2 (continued)
Entry ArCHO
Reaction Product time
6
CHO
40 min
F
Yield (%)b
Entry ArCHO
64
13
Reaction Product time
Yield (%)b
2h
CHO
CF3
F
54
O O
CF3
N H
N H 14
63
O
F
CHO
20 min
85
O
F
O
O
NH N H
NH N H
Se
2g 8
CHO
20 min
Se
2m
50 min
CHO
NH
Se
2f 7
O
NH
O
Se
2n 86
CHO
15
CHO
O
2 hr
53
O
F Me 9
O
Br 40 min
CHO
Br
72
NH
O N H
O
Br
NH
O N H
Se
2o 16
Se
CHO
1.5 h
52
2i 10
CHO
35 min
66
Br
O NH
O
Br
N H
O NH
O N H
2p 17
Se
30 min
S
60
S
CHO
O
2j 11
CHO
30 min
NO2
NH
O
48
N H
O NO2
N H
18
Se
Br
1h
S
CHO
S O
50 min
CN
46
NH
O N H
O CN
a
N H
Se
Se
2r
NH
O
2l
50
Br
CHO
2k 12
Se
2q
NH
O
Se
General reaction conditions: Ethyl acetoacetate (3mL) aryl aldehyde (0.75 mmol), selenourea (61 mg, 0,75 mmol), Hf(OTf)4 (5 mol%), 120 °C. b Isolated yield.
990
P. Chen, M. Tu / Tetrahedron Letters 59 (2018) 987–990
A. Supplementary data Supplementary data associated with this article can be found, in the online version, at https://doi.org/10.1016/j.tetlet.2018.01.070.
7.
References 1. (a) Hutton JG. J Am Chem Soc. 1931;23:1076; (b) Franke KW. J Nutr. 1934;8:597; (c) Franke KW. J Nutr. 1934;8:609; (d) Franke KW, Potter VR. J Nutr. 1934;8:615; (e) Franke KW. J Nutr. 1935;10:223; (f) Franke KW, Painter EP. J Nutr. 1935;10:599. 2. (a) Combs GF. BioFactors. 2000;12:39; (b) Zimmerman MB, Kohrle J. Thyroid. 2000;12:867. 3. (a) Cahn RS, Ingold CK, Prelog V. Angew Chem Int Ed. 1966;5:385; (b) Huber RE, Criddle RS. Arch Biochem Biophys. 1967;122:164; (c) Prelog V, Helmchen G. Angew Chem Int Ed. 1982;21:567; (d) Jacob C, Giles GI, Giles NM, Sies H. Angew Chem Int Ed. 2003;42:4742. 4. (a) Wu ZP, Hilvert D. J Am Chem Soc. 1989;111:4513; (b) Wilson SR, Zucker PA, Huang R-C, Spector A. J Am Chem Soc. 1989;111:5936; (c) Andersson CM, Hallberg A, Brattsand R, Cotgreave IA, Engman L, Persson J. Bioorg Med Chem Lett. 1993;3:2553; (d) Iwaoka M, Tomoda S. J Am Chem Soc. 1994;116:2557; (e) Galet V, Bernier J, Hénichart L, et al. J Med Chem. 1994;37:2903; (f) Wirth T. Molecules. 1998;3:164; (g) Mugesh G, Panda A, Singh HB, Punekar NS, Butcher RJ. J Am Chem Soc. 2001;123:839; (h) Jauslin ML, Wirth T, Meier T, Schoumacher F. Hum Mol Genet. 2002;11:3055; (i) Zade SS, Panda S, Tripathi SK, Singh HB, Wolmershaeuser GE. Eur J Org Chem. 2004;18:3857; (j) Sun Y, Mu Y, Ma S, et al. BBA. 2005;1743:199; (k) Sarma BK, Manna D, Minoura M, Mugesh G. J Am Chem Soc. 2010;132:5364. 5. (a) Aron ZD, Overman LE. J Am Chem Soc. 2005;127:3380; (b) Arnold MA, Day KA, Duron SG, Gin DY. J Am Chem Soc. 2006;128:13255. 6. (a) Lewis RW, Mabry J, Polisar JG, Eagen KP, Ganem B, Hess GP. Biochemistry. 2010;49:4841; (b) Zhu X, Zhao G, Zhou X, et al. Bioorg Med Chem Lett. 2010;20:299; (c) Dhumaskar KL, Meena SN, Ghadi SC, Tilve SG. Bioorg Med Chem Lett. 2014;24:2897; (d) Treptow TGM, Figueir F, Jandre EHF, et al. Eur J Med Chem. 2015;95:552; (e) Chikhale R, Menghani S, Babu R, et al. Eur J Med Chem. 2015;96:30;
8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25. 26. 27.
(f) Rashid U, Sultana R, Shaheen N, et al. Eur J Med Chem. 2016;115:230; (g) Singh K, Kaur T. MedChemCommun. 2016;7:749. (a) Some recent reviews of Biginelli reaction, see Wu X, Gong L. In: Zhu J, Wang M, Wang M, eds. Multicomponent Reactions in Organic Synthesis. Boschstr. 12, 69469 Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA; 2015:439–467. ch.15; (b) Suresh, Sandhu JS. ARKIVOC. 2012;66; (c) Panda SS, Khanna P, Khanna L. Curr Org Chem. 2012;16:507; (d) Heravi MM, Asadi S, Lashkariani BM. Mol Divers. 2013;17:389; (e) Tao L, Zhu C, Wei Y, Zhao Y. Adv Polym Sci. 2015;269:43; (f) Herrera RP, Marques-Lopez E. In: Herrera RP, Marques-Lopez E, eds. Multicomponent Reactions: Concepts and Applications for Design and Synthesis. New Jersey: John Wiley & Sons Inc; 2015:306–330. Ch. 9; (g) Fatima A, Braga TC, Neto LS, et al. J Adv Res. 2015;6:363; (h) Fatima A, Terra BS, Neto LS, Braga TC. In: Brahmachari G, ed. Green Synthetic Approaches for Biologically Relevant Heterocycles. Netherlands: Elsevier Inc; 2015:317–337. Ch. 12; (i) Nagarajaiah H, Mukhopadhyay A, Moorthy JN. Tetrahedron Lett. 2016;57:5135. Klein E, DeBonis S, Thiede B, Skoufias DA, Frank Kozielski F, Lebeau L. Bioorg Med Chem. 2007;15:6474. Lu J, Bai Y, Wang Z, Yang B, Ma H. Tetrahedron Lett. 2000;41:9075. Fu NY, Yuan YF, Cao Z, Wang SW, Wang JT, Peppe C. Tetrahedron. 2002;58:4801. Lu J, Bai Y. Synthesis. 2002;466. Maiti G, Kundu P, Guin C. Tetrahedron Lett. 2003;44:2757. Bose DS, Fatima L, Mereyala HB. J Org Chem. 2003;68:587. Gohain M, Prajapati D, Sandhu JS. Synlett. 2004;235. Narsaiah AV, Basak AK, Nagaiah K. Synthesis. 2004;1253. Jenner G. Tetrahedron Lett. 2004;45:6195. Han X, Xu F, Luo Y, Shen Q. Eur J Org Chem. 2005;1500. El Badaoui H, Bazi F, Tahir R, Lazrek HB, Sebti S. Catal Commun. 2005;6:455. Kalita HR, Phukan P. Catal Commun. 2007;8:179. Saini A, Kumar S, Sandhu JS. Indian J Chem B. 2007;46:1690. Li D, Mao H, An L, Zhao Z, Zou J. Chin J Chem. 2010;28:2025. Ladole CA, Salunkhe NG, Aswar AS. J Indian Chem Soc. 2016;93:337. Yuan H, Zhang K, Xia J, Hu X, Yuan S. Cogent Chem. 2017;3 1318692. (a) Hachiya I, Moriwaki M, Kobayashi S. Bull Chem Soc Jpn. 1995;68:2053–2060; (b) Shiina I, Suzuki M. Tetrahedron Lett. 2002;43:6391–6394. Kobayashi S, Moriwaki M, Hachiya I. Tetrahedron Lett. 1996;37:2053. Perin G, Mello LG, Radatz CS. Tetrahedron Lett. 2010;51:4354. (a) Liu Y, Song T, Meng W, Xu Y, Wang PG, Zhao W. Tetrahedron Lett. 2016;57:2758; (b) Chen P, Zhang X. Tetrahedron Lett. 2017;58:309.
Contents lists available at ScienceDirect
Tetrahedron Letters journal homepage: www.elsevier.com/locate/tetlet
Synthesis of 2-selenoxo DHPMs by Biginelli reaction with Hf(OTf)4 as catalyst Peiran Chen a,b,⇑, Mengdi Tu a a b
Donghua University, 2999 Renmin Road North, Songjiang District, Shanghai 201620, China Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032, China
a r t i c l e
i n f o
a b s t r a c t
Article history: Received 24 November 2017 Revised 22 January 2018 Accepted 23 January 2018 Available online 31 January 2018
By using Hf(OTf)4 as catalyst, a series of 2-selenoxo DHPMs have been synthesized efficiently in good yields by Biginelli reaction with selenourea as starting material. Ó 2018 Elsevier Ltd. All rights reserved.
Keywords: Hf(OTf)4 Selenourea 2-Selenoxo DHPMs Biginelli reaction
Since found in 1818, selenium was known as poison for a long time because of the health problems that it might lead to -such as livestock disease and intoxication.1 After in-depth study on its biological and pharmaceutical activities in the passing decades, selenium is now considered as an essential micronutrient element for mammals.2 More and more researches have been carried out on the preparation and bio-activities of seleno-containing compounds. For example, since its Sec-residue showed unique redox character, which might owe to the relative low redox potential of the selenium, selenocysteine was referred to as the 21st amino acid.3 A series of Se-containing compounds, such as ebselen and its derivatives, were synthesized as glutathione peroxidase (GPX) mimics and showed various bioactivities including anti-inflammatory, antiatherosclerotic, cytoprotective and antioxidative properties.4
H2N
O SeH COOH
L-Selenocysteine
N Ph Se ebselen
⇑ Corresponding author at: Donghua University, 2999 Renmin Road North, Songjiang District, Shanghai 201620, China. E-mail address: [email protected] (P. Chen). https://doi.org/10.1016/j.tetlet.2018.01.070 0040-4039/Ó 2018 Elsevier Ltd. All rights reserved.
3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) and their derivatives – which present in wide ranging natural products such as marine alkaloids5 – have attracted more and more attention since their broad spectrum of pharmacological activities such as antiviral, antitumour, antibacterial, antimalarial, antitubercular, antidiabetic, antiepileptic, antiproliferative activities, etc.6 As one of the most important multicomponent reactions (MCRs), Biginelli reaction provides an easy and effective process to prepare DHPMs (Scheme 1).7 Till now, the investigation of DHPMs, whether on preparation or on bio-activities, were focused on 2-oxo or 2-thioxo DHPMs. So far, the synthesis of 2-selenoxo DHPMs was rarely mentioned.8 As reported, the acid catalyst played a key role in the first step of Biginelli reaction to promotion the combination of aromatic aldehydes with urea.7i A wide range of Lewis acid catalysts such as SmI2,9 LaCl37H2O,10 CuSO45H2O,11 ZnCl2,12 ZnI2,13 CuI,14 GaI3,15 GaBr3/GaCl3,16 LiBr,17 InBr3,18 CdCl2,19 CeCl37H2O,20 FeCl36H2O/NiCl26H2O/HCl,21 NiFe2O4,22 GaCl323 have been reported to be used in Biginelli reaction for the preparation of 2-oxo or 2thio DHPMs. Recently, as an efficient Lewis acid catalyst, Hf(OTf)4 has been used to promote Friedel-Crafts reaction,24 Fries rearrangement,25 thioacetalization reaction26 and Ferrier rearrangement.27 Herein, we report our research for the preparation of 2-selenoxo-DHPMs by Biginelli reaction with Hf(OTf)4 as an efficient Lewis acid catalyst. First of all, we compared a series of the rare earth motel triflate for the catalytic efficiency. Reaction condition optimization was
988
P. Chen, M. Tu / Tetrahedron Letters 59 (2018) 987–990
O
O
O/S OR
+ ArCHO +
H2 N
O acid condition
Ar NH
O
NH2
N H
O/S
Scheme 1.
Table 1 Comparation of several Lewis acid catalysts in the Biginelli reaction using selenourea as starting material.a
Table 2 Preparation of 2-selenoxo DHPMs with Biginelli reaction promoted by Hf(OTf)4.a
O O
O O H3C
O
Se
+ PhCHO + OEt
catalyst
H2N
NH2
NH
O
120oC
N H
H3C
O
Se
+ ArCHO + H2N
OEt
NH2
Hf(OTf)4
Ar NH
O
120oC
N H
Se
Se
Entry
Catalyst
Reaction time
Conversion (%)b
1 2 3 4 5
In(OTf)3 Y(OTf)3 Hf(OTf)4 Yb(OTf)3 Sm(OTf)3
24 h 24 h 1h 24 h 24 h
Trace Trace 78 Trace Trace
a Reaction conditions: Ethyl acetoacetate(3mL) benzaldehyde (80 mg, 0.75 mmol), selenourea (61 mg, 0,75 mmol), cat. (5 mol%), 120 °C. b Isolated yield.
performed. Among In(OTf)3, Y(OTf)3, Sm(OTf)3, Hf(OTf)4 and Yb (OTf)3 we found Hf(OTf)4 was the most efficient (Table 1). With Hf(OTf)4 as the catalyst, a series of 2-selenoxo-DHPMs was performed with b-ketoester, selenourea, and various aryl aldehydes. Results of reaction were shown in Table 2. In our reaction system, a series of 2-selenoxo-DHPMs could be afforded in good yields. Selenourea showed relatively low reactive activity in Biginelli reaction, therefore higher reaction temperature (120 °C) was necessary. The aromatic aldehydes with electron-donating group (Table 2, entries 2–5) gave the corresponding DHPMs in higher yields than those with electron-withdrawing group at the same position (Table 2, entries 6, 7, 9–12). Moreover, naphthaldehyde and thiophenecarboxaldehyde also could afford the corresponding DHPMs effectively under the same conditions smoothly (Table 2, entries 14, 17, and 18), but the heteroatom on the aromatic ring of the aryl aldehyde might cause the decreasing of the yield. More b-dicarbonyl compounds, including methyl acetoacetate, t-butyl acetoacetate, benzyl acetoacetate, ethyl trifluoroacetoacetate, ethyl propionoacetoacetate and 2,4-pentanedione, have been tested as substrate in our Biginelli reaction system. But none of those b-dicarbonyl compounds afforded the required DHPMs. Ethyl trifluoroacetoacetate gave the by-product which might be formed in Knoevenagel route. No improvement could be achieved while the reaction temperature was elevated to 150 °C. Therefore, ethyl acetoacetate seems to be the best substrate for our reaction system. In summary, we have developed an efficient catalytic system for Biginelli reaction to synthesize 2-selenoxo DHPMs, which includes aryl aldehydes, ethyl acetoacetate, and selenourea as starting material and Hf(OTf)4 as the catalyst. Under our reaction conditions, corresponding 2-selenoxo DHPMs were afforded in moderate to excellent yields.
Entry ArCHO 1
CHO
Reaction Product time
Yield (%)b
1h
81
O NH
O N H
Se
2a 2
CHO
40 min
85
O
Me
Me NH
O N H
Se
2b CHO 40 min
3
73
OMe
MeO
O O
NH N H
Se
2c 4
CHO
10 min
OPh
94
O OPh
O
NH N H
Se
2d CHO 30 min
5
71
SMe
MeS
O NH
O N H
2e
Se
989
P. Chen, M. Tu / Tetrahedron Letters 59 (2018) 987–990 Table 2 (continued)
Table 2 (continued)
Entry ArCHO
Reaction Product time
6
CHO
40 min
F
Yield (%)b
Entry ArCHO
64
13
Reaction Product time
Yield (%)b
2h
CHO
CF3
F
54
O O
CF3
N H
N H 14
63
O
F
CHO
20 min
85
O
F
O
O
NH N H
NH N H
Se
2g 8
CHO
20 min
Se
2m
50 min
CHO
NH
Se
2f 7
O
NH
O
Se
2n 86
CHO
15
CHO
O
2 hr
53
O
F Me 9
O
Br 40 min
CHO
Br
72
NH
O N H
O
Br
NH
O N H
Se
2o 16
Se
CHO
1.5 h
52
2i 10
CHO
35 min
66
Br
O NH
O
Br
N H
O NH
O N H
2p 17
Se
30 min
S
60
S
CHO
O
2j 11
CHO
30 min
NO2
NH
O
48
N H
O NO2
N H
18
Se
Br
1h
S
CHO
S O
50 min
CN
46
NH
O N H
O CN
a
N H
Se
Se
2r
NH
O
2l
50
Br
CHO
2k 12
Se
2q
NH
O
Se
General reaction conditions: Ethyl acetoacetate (3mL) aryl aldehyde (0.75 mmol), selenourea (61 mg, 0,75 mmol), Hf(OTf)4 (5 mol%), 120 °C. b Isolated yield.
990
P. Chen, M. Tu / Tetrahedron Letters 59 (2018) 987–990
A. Supplementary data Supplementary data associated with this article can be found, in the online version, at https://doi.org/10.1016/j.tetlet.2018.01.070.
7.
References 1. (a) Hutton JG. J Am Chem Soc. 1931;23:1076; (b) Franke KW. J Nutr. 1934;8:597; (c) Franke KW. J Nutr. 1934;8:609; (d) Franke KW, Potter VR. J Nutr. 1934;8:615; (e) Franke KW. J Nutr. 1935;10:223; (f) Franke KW, Painter EP. J Nutr. 1935;10:599. 2. (a) Combs GF. BioFactors. 2000;12:39; (b) Zimmerman MB, Kohrle J. Thyroid. 2000;12:867. 3. (a) Cahn RS, Ingold CK, Prelog V. Angew Chem Int Ed. 1966;5:385; (b) Huber RE, Criddle RS. Arch Biochem Biophys. 1967;122:164; (c) Prelog V, Helmchen G. Angew Chem Int Ed. 1982;21:567; (d) Jacob C, Giles GI, Giles NM, Sies H. Angew Chem Int Ed. 2003;42:4742. 4. (a) Wu ZP, Hilvert D. J Am Chem Soc. 1989;111:4513; (b) Wilson SR, Zucker PA, Huang R-C, Spector A. J Am Chem Soc. 1989;111:5936; (c) Andersson CM, Hallberg A, Brattsand R, Cotgreave IA, Engman L, Persson J. Bioorg Med Chem Lett. 1993;3:2553; (d) Iwaoka M, Tomoda S. J Am Chem Soc. 1994;116:2557; (e) Galet V, Bernier J, Hénichart L, et al. J Med Chem. 1994;37:2903; (f) Wirth T. Molecules. 1998;3:164; (g) Mugesh G, Panda A, Singh HB, Punekar NS, Butcher RJ. J Am Chem Soc. 2001;123:839; (h) Jauslin ML, Wirth T, Meier T, Schoumacher F. Hum Mol Genet. 2002;11:3055; (i) Zade SS, Panda S, Tripathi SK, Singh HB, Wolmershaeuser GE. Eur J Org Chem. 2004;18:3857; (j) Sun Y, Mu Y, Ma S, et al. BBA. 2005;1743:199; (k) Sarma BK, Manna D, Minoura M, Mugesh G. J Am Chem Soc. 2010;132:5364. 5. (a) Aron ZD, Overman LE. J Am Chem Soc. 2005;127:3380; (b) Arnold MA, Day KA, Duron SG, Gin DY. J Am Chem Soc. 2006;128:13255. 6. (a) Lewis RW, Mabry J, Polisar JG, Eagen KP, Ganem B, Hess GP. Biochemistry. 2010;49:4841; (b) Zhu X, Zhao G, Zhou X, et al. Bioorg Med Chem Lett. 2010;20:299; (c) Dhumaskar KL, Meena SN, Ghadi SC, Tilve SG. Bioorg Med Chem Lett. 2014;24:2897; (d) Treptow TGM, Figueir F, Jandre EHF, et al. Eur J Med Chem. 2015;95:552; (e) Chikhale R, Menghani S, Babu R, et al. Eur J Med Chem. 2015;96:30;
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