Synthesis of Substituted Indole-3-carboxylates by Iron(II)-Catalyzed Domino Isomerization of 3-Alkyl/aryl-4-aryl-5-methoxyisoxazoles

Abstract

The iron(II)-catalyzed domino isomerization of 3-alkyl/aryl-4-arylisoxazoles provides a selective access to a wide range of structurally diverse highly substituted indole-3-carboxylates. The operational simplicity, high atom efficiency, and the use of stable starting materials and an inexpensive and low-toxicity catalyst are some of the attractive features of this tandem double ring-opening–ring-closure strategy.

Key words

indoles - isoxazoles - isomerization - domino reactions - iron(II) chloride catalysis

• References

• 1 Gribble GW. Indole Ring Synthesis: From Natural Products to Drug Discovery. John Wiley & Sons; Chichester: 2016

For reviews, see:
• 2a Baumann M. Baxendale IR. Ley SV. Nikbin N. Beilstein J. Org. Chem. 2011; 7: 442
• 2b Kaushik NK. Kaushik N. Attri P. Kumar N. Kim CH. Verma AK. Choi EH. Molecules 2013; 18: 6620
• 2c Zhang M.-Z. Chen Q. Yang G.-F. Eur. J. Med. Chem. 2015; 89: 421
• 2d Gale PA. Chem. Commun. 2008; 4525

For reviews, see:
• 3a Humphrey GR. Kuethe JT. Chem. Rev. 2006; 106: 2875
• 3b Vicente R. Org. Biomol. Chem. 2011; 9: 6469
• 3c Taber DF. Tirunahari PK. Tetrahedron 2011; 67: 7195
• 3d Bartoli G. Dalpozzo R. Nardi M. Chem. Soc. Rev. 2014; 43: 4728
• 3e Pozharskii AF. Kachalkina SG. Gulevskaya AV. Filatova EA. Russ. Chem. Rev. 2017; 86: 589
• 3f Heravi MM. Rohani S. Zadsirjan V. Zahedi N. RSC Adv. 2017; 7: 52852
• 4 Ahluwalia VK. Kidwai M. New Trends in Green Chemistry 2004
• 5 Kern N. Hoffmann M. Blanc A. Weibel J.-M. Pale P. Org. Lett. 2013; 15: 836
• 6a Khlebnikov AF. Novikov MS. Top. Heterocycl. Chem. 2016; 41: 143
• 6b Huang C.-Y. Doyle AG. Chem. Rev. 2014; 114: 8153
• 6c Khlebnikov AF. Novikov MS. Tetrahedron 2013; 69: 3363
• 6d Padwa A. Adv. Heterocycl. Chem. 2010; 99: 1
• 7a Isomura K. Kobayashi S. Taniguchi H. Tetrahedron Lett. 1968; 9: 3499
• 7b Isomura K. Uto K. Taniguchi H. J. Chem. Soc., Chem. Commun. 1977; 664
• 7c Padwa A. Carlsen PH. J. J. Org. Chem. 1978; 43: 2029
• 7d Isomura K. Ayabe G.-I. Hatano S. Taniguchi H. J. Chem. Soc., Chem. Commun. 1980; 1252
• 7e Taber DF. Tian W. J. Am. Chem. Soc. 2006; 128: 1058
• 7f Chiba S. Hattoti G. Narasaka K. Chem. Lett. 2007; 36: 52
• 7g Li X. Du Y. Liang Z. Li X. Pan Y. Zhao K. Org. Lett. 2009; 11: 2643
• 7h Jana S. Clements MD. Sharp BK. Zheng N. Org. Lett. 2010; 12: 3736
• 8a Galenko EE. Khlebnikov AF. Novikov MS. Chem. Heterocycl. Compd. 2016; 52: 637
• 8b Auricchio S. Bini A. Pastormerlo E. Truscello AM. Tetrahedron 1997; 53: 10911
• 8c Mikhailov KI. Galenko EE. Galenko AV. Novikov MS. Ivanov AYu. Starova GL. Khlebnikov AF. J. Org. Chem. 2018; 83: 3177
• 8d Galenko EE. Bodunov VA. Galenko AV. Novikov MS. Khlebnikov AF. J. Org. Chem. 2017; 82: 8568
• 8e Galenko AV. Galenko EE. Shakirova FM. Novikov MS. Khlebnikov AF. J. Org. Chem. 2017; 82: 5367
• 8f Galenko EE. Galenko AV. Khlebnikov AF. Novikov MS. Shakirova JR. J. Org. Chem. 2016; 81: 8495
• 8g Galenko EE. Tomashenko OA. Khlebnikov AF. Novikov MS. Panikorovskii TL. Beilstein J. Org. Chem. 2015; 11: 1732
• 8h Galenko EE. Tomashenko OA. Khlebnikov AF. Novikov MS. Org. Biomol. Chem. 2015; 13: 9825
• 8i Galenko EE. Galenko AV. Khlebnikov AF. Novikov MS. RSC Adv. 2015; 5: 18172
• 9 Bauer I. Knölker H.-J. Chem. Rev. 2015; 115: 3170
• 10 Wu C. Li J. Yan B. Dalton Trans. 2014; 43: 5364
• 11 Dannhardt G. Laufer S. Obergrusberger I. Synthesis 1989; 275
• 12 Scarpati R. Gazz. Chim. Ital. 1959; 89: 1511
• 13 Davis FA. J. Org. Chem. 1999; 64: 8929
• 14 Zhou L. Doyle M. J. Org. Chem. 2009; 74: 9222
• 15 Tanimori S. Ura H. Kirihata M. Eur. J. Org. Chem. 2007; 3977
• 16 Kaneko C. Fujii H. Kawai S. Hashiba K. Karasawa Y. Wakai M. Hayashi R. Somei M. Chem. Pharm. Bull. 1982; 30: 74
• 17 Zhang X. Zhang-Negrerie D. Deng J. Du Y. Zhao K. J. Org. Chem. 2013; 78: 12750