Synthesis 2017; 49(23): 5251-5257
DOI: 10.1055/s-0036-1588486
paper
© Georg Thieme Verlag Stuttgart · New York

Domino Reactions of 1-Aroyl-3,4-dihydroisoquinolines with α,β-Unsaturated Aldehydes

Maria D. Matveeva
a   Peoples’ Friendship University of Russia (RUDN University), 6, Mikluho-Maklaya St., Moscow 117198, Russian Federation   Email: lvoskressensky@sci.pfu.edu.ru
,
Tatiana N. Borisova
a   Peoples’ Friendship University of Russia (RUDN University), 6, Mikluho-Maklaya St., Moscow 117198, Russian Federation   Email: lvoskressensky@sci.pfu.edu.ru
,
Alexander A. Titov
a   Peoples’ Friendship University of Russia (RUDN University), 6, Mikluho-Maklaya St., Moscow 117198, Russian Federation   Email: lvoskressensky@sci.pfu.edu.ru
,
Lada V. Anikina
b   Institute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka, Russian Federation
,
Svetlana V. Dyachenko
a   Peoples’ Friendship University of Russia (RUDN University), 6, Mikluho-Maklaya St., Moscow 117198, Russian Federation   Email: lvoskressensky@sci.pfu.edu.ru
,
Grigorii S. Astakhov
a   Peoples’ Friendship University of Russia (RUDN University), 6, Mikluho-Maklaya St., Moscow 117198, Russian Federation   Email: lvoskressensky@sci.pfu.edu.ru
,
Alexey V. Varlamov
a   Peoples’ Friendship University of Russia (RUDN University), 6, Mikluho-Maklaya St., Moscow 117198, Russian Federation   Email: lvoskressensky@sci.pfu.edu.ru
,
Leonid G. Voskressensky*
a   Peoples’ Friendship University of Russia (RUDN University), 6, Mikluho-Maklaya St., Moscow 117198, Russian Federation   Email: lvoskressensky@sci.pfu.edu.ru
› Author Affiliations
This work was supported by the Russian Foundation for Basic Research (grant 17-03-00605) and was financially supported by the Ministry of Education and Science of the Russian Federation (agreement no. 02.a03.21.0008).
Further Information

Publication History

Received: 16 April 2017

Accepted after revision: 12 June 2017

Publication Date:
22 August 2017 (online)


Abstract

An efficient synthesis of pyrrolo[2,1-a]isoquinolines by a domino reaction from a variety of 3,4-dihydropyrrolo[2,1-a]isoquinolines and α,β-unsaturated aldehydes in the absence of catalyst in good yields under microwave irradiation, is reported.

Supporting Information

 
  • References

    • 1a Ranu BC. Banerjee S. Tetrahedron Lett. 2007; 48: 141
    • 1b Ying A.-G. Liu L. Wu G.-F. Chen G. Chen X.-Z. Ye W.-D. Tetrahedron Lett. 2009; 50: 1653
    • 1c Verma S. Mungse HP. Kumar N. Choudhary S. Jain SL. Sain B. Khatri OP. Chem. Commun. 2011; 12673
    • 1d Li L. Liu Z. Ling Q. Xing X. J. Mol. Catal. A: Chem. 2012; 353-354: 178
    • 1e Tamaddon F. Tayefi M. Hosseini E. Zare E. J. Mol. Catal. A: Chem. 2013; 366: 36
    • 2a Goff RL. Lawson AM. Daïch А. Comesse S. Org. Biomol. Chem. 2013; 11: 1818
    • 2b Görmen M. Goff RL. Lawson AM. Daïch A. Comesse S. Tetrahedron Lett. 2013; 54: 2174
    • 2c Khong SN. Kwon O. Molecules 2012; 17: 5626
    • 2d Kim S. Kang KT. Kim SG. Tetrahedron 2014; 70: 5114
    • 3a Shairgojray BA. Dar AA. Bhat BA. Tetrahedron Lett. 2013; 54: 2391
    • 3b Ghandi M. Feizi S. Ziaie F. Notash B. Tetrahedron 2014; 70: 2563
    • 3c Barbier V. Couty F. David OR. P. Eur. J. Org. Chem. 2015; 3679
  • 4 Basavaiah D. Veeraraghavaiah G. Badsara SS. Org. Biomol. Chem. 2014; 12: 1551
  • 5 Ewing J. Hughes G. Ritchie E. Taylor WC. Nature 1952; 169: 618
    • 6a Andersen RJ. Faulkner DJ. He CH. Vanduyne GD. Clardy J. J. Am. Chem. Soc. 1985; 107: 5492
    • 6b Shen L. Xie N. Yang B. Hu Y. Zhang Y. Eur. J. Med. Chem. 2014; 85: 807
    • 7a Niewoehner U. Bauser M. Ergueden J.-K. Flubacher D. Naab P. Repp T.-O. Stoltefuss J. Burkhardt N. Sewing A. Schauer M. Schlemmer K.-H. Weber O. Boyer S. Miglarese M. WO Patent 02/48144, 2002
    • 7b Zhang C. Fan D. Wang Y. Li T. Boyer S. Burke J. Raudenbush B. Wong W. Ying S. Wang M. Zhao Q. Carter CA. Burkhardt N. Pernerstorfer J. Niewoehner M. Niewoehner U. WO Patent 03/051877, 2003
    • 7c Reyes-Gutiérrez PE. Camacho JR. Ramírez-Apan Ma T. Osornio YM. Martínez R. Org. Biomol. Chem. 2010; 8: 4374
  • 8 van Rijn RD. Loozen HJ. J. Timmers CM. Anders var der Veen L. Karstens WF. J. US patent 8394789, 2013
  • 9 Prabhu G. Agarwal S. Sharma V. Madurkar SM. Munshi P. Singh S. Sen S. Eur. J. Med. Chem. 2015; 95: 41
  • 10 Kakhki S. Shahosseini S. Zarghi A. Iran J. Pharm. Res. 2014; 13: 71
    • 11a Ma J. Yuan X. Küçüköz B. Li S. Zhang C. Majumdar P. Karatay A. Li X. Yaglioglu HG. Elmali A. Zhao J. Hayvali M. J. Mater. Chem. C 2014; 2: 3900
    • 11b Nekkanti S. Kumar NP. Sharma P. Kamal A. Nachtigall FM. Forero-Doria O. Santos LS. Shankaraiah N. RSC Adv. 2016; 6: 2671
    • 11c Fujiya A. Tanaka M. Yamaguchi E. Tada N. Itoh A. J. Org. Chem. 2016; 81: 7262
    • 12a Sun L.-L. Liao Z.-Y. Tang R.-Y. Deng C.-L. Zhang X.-G. J. Org. Chem. 2012; 77: 2850
    • 12b Cheng T. Meng S. Huang Y. Org. Lett. 2013; 15: 1958
    • 12c Tang X. Huang L. Qi C. Wu W. Jiang H. Chem. Commun. 2013; 9597
    • 12d Wiest JM. Pöthig A. Bach T. Org. Lett. 2016; 18: 852
  • 13 Cho S.-D. Kweon D.-H. Kang Y.-J. Lee S.-G. Lee WS. Yoon Y.-J. J. Heterocycl. Chem. 1999; 36: 1151
  • 14 Awuah E. Capretta A. J. Org. Chem. 2010; 75: 5627
  • 15 Shklyaev YuV. Yeltsov MA. Rozhkova YuS. Tolstikov AG. Dembitsky VM. Heteroat. Chem. 2004; 15: 486
  • 16 Xie WD. Li PL. Jia ZJ. Pharmazie 2005; 60: 233
  • 17 García MD. Wilson AJ. Emmerson DP. G. Jenkins PR. Chem. Commun. 2006; 2586