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Volumn , Issue 8, 2008, Pages 1159-1164

Synthesis of isoquinoline-3-carboxylates and benzocyclobutanes via reaction of 2-amidoacrylate esters with arynes

Author keywords

2 amidoacrylate esters; Annulations; Arynes; Benzocyclobutanes; Isoquinoline heterocycles

Indexed keywords

BENZOCYCLOBUTANE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLOBUTANE DERIVATIVE; DEHYDROALANINE; ESTER; ISOQUINOLINE 3 CARBOXYLIC ACID;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DEHYDRATION; SYNTHESIS;

EID: 44349185397 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072723 Document Type: Article

Times cited : (35)

References (19)

1
- 33746281785
- For reviews on the use of arynes in organic synthesis, see: a
- For reviews on the use of arynes in organic synthesis, see: (a) Peña, D.; Pérez, D.; Guitián, E. Angew. Chem. Int. Ed. 2006, 45, 3579.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 3579
- Peña, D.¹ Pérez, D.² Guitián, E.³

2
- 0000264238
- Trost, B. M, Fleming, I, Eds, Pergamon Press: New York
- (b) Kessar, S. V. Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991, 483-515.
- (1991) Comprehensive Organic Synthesis , vol.4 , pp. 483-515
- Kessar, S.V.¹

3
- 33748480130
- For the application of arynes in total synthesis, see
- (a) For the application of arynes in total synthesis, see: Tambar, U. K.; Ebner, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128, 11752.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 11752
- Tambar, U.K.¹ Ebner, D.C.² Stoltz, B.M.³

4
- 3242889915
- (b) Sato, Y.; Tamura, T.; Mori, M. Angew. Chem. Int. Ed. 2004, 43, 2436.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 2436
- Sato, Y.¹ Tamura, T.² Mori, M.³

5
- 0002977163
- Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211.
- (1983) Chem. Lett , pp. 1211
- Himeshima, Y.¹ Sonoda, T.² Kobayashi, H.³

6
- 33645768327
- and references therein
- Liu, Z. J.; Larock, R. C. J. Org. Chem. 2006, 71, 3198; and references therein.
- (2006) J. Org. Chem , vol.71 , pp. 3198
- Liu, Z.J.¹ Larock, R.C.²

7
- 17644362249
- Tambar, U. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 5340.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 5340
- Tambar, U.K.¹ Stoltz, B.M.²

8
- 22544456259
- Yoshida, H.; Watanabe, M.; Ohshita, J.; Kunai, A. Chem. Commun. 2005, 3292.
- (2005) Chem. Commun , pp. 3292
- Yoshida, H.¹ Watanabe, M.² Ohshita, J.³ Kunai, A.⁴

9
- 23944440375
- Yoshida, H.; Watanabe, M.; Ohshita, J.; Kunai, A. Tetrahedron Lett. 2005, 46, 6729.
- (2005) Tetrahedron Lett , vol.46 , pp. 6729
- Yoshida, H.¹ Watanabe, M.² Ohshita, J.³ Kunai, A.⁴

10
- 33947581843
- Ramtohul, Y. K.; Chartrand, A. Org. Lett. 2007, 9, 1029.
- (2007) Org. Lett , vol.9 , pp. 1029
- Ramtohul, Y.K.¹ Chartrand, A.²

11
- 38949175721
- 2 (TBAT) as the fluoride source in THF, see: Gilmore, C. D.; Allan, K. M.; Stoltz, B. M. J. Am. Chem. Soc. 2008, 130, 1558.
- 2 (TBAT) as the fluoride source in THF, see: Gilmore, C. D.; Allan, K. M.; Stoltz, B. M. J. Am. Chem. Soc. 2008, 130, 1558.

12
- 33745105781
- Jeganmohan, M.; Cheng, C.-H. Chem. Commun. 2006, 2454.
- (2006) Chem. Commun , pp. 2454
- Jeganmohan, M.¹ Cheng, C.-H.²

13
- 22544456259
- Yoshida, H.; Watanabe, M.; Ohshita, J.; Kunai, A. Chem. Commun. 2005, 3292.
- (2005) Chem. Commun , pp. 3292
- Yoshida, H.¹ Watanabe, M.² Ohshita, J.³ Kunai, A.⁴

14
- 44349097235
- Avenoza, A.; Cativiela, C.; Busto, J. H.; Fernández-Recio, M. A.; Peregrina, J. M.; Rodríguez, F. Tetrahedron 2001, 57, 548.
- (2001) Tetrahedron , vol.57 , pp. 548
- Avenoza, A.¹ Cativiela, C.² Busto, J.H.³ Fernández-Recio, M.A.⁴ Peregrina, J.M.⁵ Rodríguez, F.⁶

15
- 0037009032
- (a) Yoshida, H.; Shirakawa, E.; Honda, Y.; Hiyama, T. Angew. Chem. Int. Ed. 2002, 41, 3247.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 3247
- Yoshida, H.¹ Shirakawa, E.² Honda, Y.³ Hiyama, T.⁴

16
- 33748053357
- (b) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc. 2006, 128, 11040.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 11040
- Yoshida, H.¹ Fukushima, H.² Ohshita, J.³ Kunai, A.⁴

17
- 12444344925
- (a) Zhu, Y.-F.; Wilcoxen, K.; Gross, T.; Connors, P.; Strack, N.; Gross, R.; Huang, C. Q.; McCarthy, J. R.; Xie, Q.; Ling, N.; Chen, C. Bioorg. Med. Chem. Lett. 2003, 13, 1927.
- (2003) Bioorg. Med. Chem. Lett , vol.13 , pp. 1927
- Zhu, Y.-F.¹ Wilcoxen, K.² Gross, T.³ Connors, P.⁴ Strack, N.⁵ Gross, R.⁶ Huang, C.Q.⁷ McCarthy, J.R.⁸ Xie, Q.⁹ Ling, N.¹⁰ Chen, C.¹¹

18
- 0035829434
- (b) Chen, C.; Zhu, Y.-F.; Liu, X.-J.; Lu, Z.-X.; Xie, Q.; Ling, N. J. Med. Chem. 2001, 44, 4001.
- (2001) J. Med. Chem , vol.44 , pp. 4001
- Chen, C.¹ Zhu, Y.-F.² Liu, X.-J.³ Lu, Z.-X.⁴ Xie, Q.⁵ Ling, N.⁶

19
- 44349193164
- Representative Experimental Procedure To a mixture of methyl 2-acetamidoacrylate (11j, 57.3 mg, 0.4 mmol, 1 equiv) and CsF (152 mg, 1 mmol, 2.5 equiv) in dry MeCN (2 mL, 0.2 M) was added o-silyl aryltriflate (1, 121 μL, 0.5 mmol, 1.25 equiv) in an oven-dried 4 mL glass vial. The vial was capped under nitrogen and the mixture was stirred at r.t. overnight (ca. 18 h, The reaction mixture was quenched with HCl (1 N) or TFA (154 μL, 2 mmol, 5 equiv) and the solvent was evaporated. The residue was diluted with NaHCO3 (2 mL, 5, and extracted with EtOAc (3 x 1 mL, The combined EtOAc extracts were dried over Na2SO4 and concentrated. The crude product was purified by CombiFlash chromatography (ISCO) on silica gel column using a gradient elution of 30-80% EtOAc-hexanes to afford methyl 1-methylisoquinoline-3-carboxylate (12j) and methyl 7-(acetylamino) bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylate 13j, Methyl
- 3: 220.0968; found: 220.0971.

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