Electrophilic Cyclization of o-Anisole- and o-Thioanisole-Substituted Ynamides­: Synthesis of 2-Amidobenzofurans and 2-Amidobenzothiophenes

Yulong Kong; Lian Yu; Lingzi Fu; Jian Cao; Guoqiao Lai; Yuming Cui; Ziqiang Hu; Guanhai Wang

doi:10.1055/s-0033-1338481

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(14): 1975-1982
DOI: 10.1055/s-0033-1338481

paper

Electrophilic Cyclization of o-Anisole- and o-Thioanisole-Substituted Ynamides: Synthesis of 2-Amidobenzofurans and 2-Amidobenzothiophenes

Yulong Kong

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 eMail: caojian@hznu.edu.cn

,

Lian Yu

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 eMail: caojian@hznu.edu.cn

,

Lingzi Fu

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 eMail: caojian@hznu.edu.cn

,

Jian Cao*

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 eMail: caojian@hznu.edu.cn

,

Guoqiao Lai

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 eMail: caojian@hznu.edu.cn

,

Yuming Cui

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 eMail: caojian@hznu.edu.cn

,

Ziqiang Hu

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 eMail: caojian@hznu.edu.cn

,

Guanhai Wang

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Wenyi Road 222, Hangzhou 310012, P. R. of China Fax: +86(571)28865135 eMail: caojian@hznu.edu.cn

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

A facile synthesis of 3-substituted 2-amidobenzofurans and 2-amidobenzothiophenes via electrophilic cyclization reaction of o-anisole- and o-thioanisole-substituted ynamides with I₂, NBS and NCS was developed. The products 3-iodo-2-amidobenzofurans were further transferred into 3-aryl-, 3-alkynyl, and 3-vinyl-2-amidobenzofurans via Pd-catalyzed reactions such as Suzuki–Miyaura and Sonogashira cross-coupling reactions and the Heck reaction.

Key words

2-amidobenzofurans - 2-amidobenzothiophenes - electrophilic cyclization - ynamide - cross-coupling reaction

Volltext

Referenzen

References

1a Kirilmis C, Ahmedzade M, Servi S, Koca M, Kizirgil A, Kazaz C. Eur. J. Med. Chem. 2008; 43: 300
1b Schultz DM, Prescher JA, Kidd S, Marona-Lewicka D, Nichols DE, Monte A. Bioorg. Med. Chem. 2008; 16: 6242
1c Ando K, Kawamura Y, Akai Y, Kunitomo J, Yokomizo T, Yamashita M, Ohta S, Ohishi T, Ohishi Y. Org. Biomol. Chem. 2008; 6: 296
1d Dixit M, Tripathi BK, Tamrakar AK, Srivastava AK, Kumar B, Goel A. Bioorg. Med. Chem. 2007; 15: 727

2a Su T, Naughton MA. H, Smyth MS, Rose JW, Arfsten AE, McCowan JR, Jakubowski JA, Wyss VL, Ruterbories KJ, Sall DJ, Scarborough RM. J. Med. Chem. 1997; 40: 4308
2b Takeuchi K, Kohn TJ, Bastian JA, Chirgadze NY, Denney ML, Harper RW, Lin H, Mccowan JR, Gifford-Moore DS, Richett ME, Sall DJ, Smith GF, Zhang M. Bioorg. Med. Chem. Lett. 1999; 9: 759

For electrophilic cyclization chemistry, see:

3a Yue D, Yao T, Larock RC. J. Org. Chem. 2005; 70: 10292
3b Cho C.-H, Neuenswander B, Lushington G, Larock RC. J. Comb. Chem. 2008; 10: 941
3c Manarin F, Roehrs JA, Mozzaquatro Gay R, Brandão R, Menezes PH, Nogueira CW, Zeni G. J. Org. Chem. 2009; 74: 2153
3d Yao T, Yue D, Larock RC. J. Org. Chem. 2005; 70: 9985
3e Mehta S, Waldo JP, Larock RC. J. Org. Chem. 2009; 74: 1141
3f Mehta S, Larock RC. J. Org. Chem. 2010; 75: 1652
3g Godoi B, Schumacher RF, Zeni G. Chem. Rev. 2011; 111: 2937

4a Makovetskii VP, Dzvinchuk IB, Yaremko VV, Svishchuk AA. Ukr. Khim. Zh. 1979; 45: 652 ; Chem. Abstr. 1979, 91, 140672
4b King TJ, Newall CE. J. Chem. Soc. 1965; 974

5 Tatsumi R, Fujio M, Satoh H, Katayama J, Takanashi S, Hashimoto K, Tanaka H. J. Med. Chem. 2005; 48: 2678

For the synthesis of 2-amidobenzofurans, see:

6a Demerseman P, Guillaumel J, Cheutin A, Royer R. Bull. Soc. Chim. Fr. 1970; 2253
6b Carrër A, Florent J, Auvrouin E, Rousselle P, Bertounesque E. J. Org. Chem. 2011; 76: 2502
6c Einhorn JF, Demerseman P, Royer R. Synthesis 1984; 978

7 For the synthesis of 2-amidobenzothiophenes, see: Mitsuda S, Fujiwara T, Kimigafukuro K, Monguchi D, Mori A. Tetrahedron 2012; 68: 3585

8a DeKorver KA, Li H, Lohse AG, Hayashi R, Lu Z, Zhang Y, Hsung RP. Chem. Rev. 2010; 110: 5064
8b Evano G, Coste A, Jouvin K. Angew. Chem. Int. Ed. 2010; 49: 2840
8c Evano G, Jouvin K, Coste A. Synthesis 2013; 45: 17

For the synthesis of ynamides, see:

9a Frederick MO, Mulder JA, Tracey MR, Hsung RP, Huang J, Kurtz KC. M, Shen L, Douglas CJ. J. Am. Chem. Soc. 2003; 125: 2368
9b Zhang Y, Hsung RP, Tracey MR, Kurtz KC. M, Vera EL. Org. Lett. 2004; 6: 1151
9c Zhang X, Zhang Y, Huang J, Hsung RP, Kurtz KC. M, Oppenheimer J, Petersen ME, Sagamanova IK, Shen L, Tracey MR. J. Org. Chem. 2006; 71: 4170
9d Coste A, Karthikeyan G, Couty F, Evano G. Angew. Chem. Int. Ed. 2009; 48: 4381
9e Coste A, Couty F, Evano G. Org. Lett. 2009; 11: 4454
9f Hamada T, Ye X, Stahl SS. J. Am. Chem. Soc. 2008; 130: 833
9g Jia W, Jiao N. Org. Lett. 2010; 12: 2000
9h Jouvin K, Couty F, Evano G. Org. Lett. 2010; 12: 3272
9i Sueda T, Oshima A, Teno N. Org. Lett. 2011; 13: 3996
9j Laouiti A, Rammah MM, Rammah MB, Marrot J, Couty F, Evano G. Org. Lett. 2012; 14: 6
9k Jouvin K, Heimburger J, Evano G. Chem. Sci. 2012; 3: 756
9l Laouiti A, Jouvin K, Bourdreux F, Rammah MM, Rammah MB, Evano G. Synthesis 2012; 44: 1491

For recent reports on the reactions of ynamides, see:

10a Kramer S, Dooleweerdt K, Lindhardt AT, Rottländer M, Skrydstrup T. Org. Lett. 2009; 11: 4208
10b Shindoh N, Takemoto Y, Takasu K. Chem. Eur. J. 2009; 15: 7026
10c Cao J, Kong Y, Deng Y, Lai G, Cui Y, Hu Z, Wang G. Org. Biomol. Chem. 2012; 10: 9556
10d Yao P.-Y, Zhang Y, Hsung RP, Zhao K. Org. Lett. 2008; 10: 4275
10e Gati W, Rammah MM, Rammah MB, Couty F, Evano G. J. Am. Chem. Soc. 2012; 134: 9078
10f Cao J, Xu Y, Kong Y, Cui Y, Hu Z, Wang G, Deng Y, Lai G. Org. Lett. 2012; 14: 38
10g Garcia P, Moulin S, Miclo Y, Leboeuf D, Gandon V, Aubert C, Malacria M. Chem. Eur. J. 2009; 15: 2129
10h Garcia P, Evanno Y, George P, Sevrin M, Ricci G, Malacria M, Aubert C, Gandon V. Org. Lett. 2011; 13: 2030

11 Oppenheimer J, Johnson WL, Tracey MR, Hsung RP, Yao P.-Y, Liu R, Zhao K. Org. Lett. 2007; 9: 2361
12 Dooleweerdt K, Ruhland T, Skrydstrup T. Org. Lett. 2009; 11: 221
13 Kong Y, Jiang K, Cao J, Fu L, Yu L, Lai G, Cui Y, Hu Z, Wang G. Org. Lett. 2013; 15: 422
14 Palisse A, Kirsch SF. Org. Biomol. Chem. 2012; 10: 8041

Zusatzmaterial

Supporting Information

Electrophilic Cyclization of o-Anisole- and o-Thioanisole-Substituted Ynamides­: Synthesis of 2-Amidobenzofurans and 2-Amidobenzothiophenes

Electrophilic Cyclization of o-Anisole- and o-Thioanisole-Substituted Ynamides: Synthesis of 2-Amidobenzofurans and 2-Amidobenzothiophenes