SYNTHESIS OF 3,3-DIALKYL-1-(2-FURYL)-3,4-DIHYDROISOQUINOLINES AND THEIR REACTION WITH MALEIC ANHYDRIDE

Authors

  • А. Г. Михайловский Perm State Pharmaceutical Academy
  • З. Г. Алиев Institute of Problems of Chemical Physics, Russian Academy of Sciences
  • О. В. Сурикова Perm State Pharmaceutical Academy
  • Н. Г. Ефремова Perm State Pharmaceutical Academy

DOI:

https://doi.org/10.1007/881

Keywords:

2-cyanofuran, dialkylbenzylcarbinols, 2, 2-dialkyl-4-(2-furyl)-1, 2-dihydrobenzo[f]isoquinolines, 3, 3-dialkyl-1 (2-furyl)-3, 4-dihydroisoquinoline, exo-19, 19-dimethyl-1-(2-furyl)-15-oxa-18-azapentacyclo[10.5.2.02, 11.04, 9.013, 17]nonadeca-2, 4, 6, 8, 10-pentaene-14, 16-dione, maleic anhydride, naphthalene derivatives, cyclocondensation

Abstract

The cyclocondensation of dialkylbenzylcarbinols with 2-cyanofuran in the presence of H2SO4 gave 3,3‑dialkyl-1-(2-furyl)-3,4-dihydroisoquinolines. Analogously, naphthalene derivatives form 4-(2-furyl)benzo[f]isoquinolines. The Diels–Alder reaction of 2,2-dimethyl-4-(2-furyl)-1,2-dihydrobenzo[f]isoquinoline with maleic anhydride proceeds at N(1) and C(4) of the isoquinoline system to give exo-19,19-dimethyl-1-(2-furyl)-15-oxa-18-azapentacyclo[10.5.2.02,11.04,9.013,17]nonadeca-2,4,6,8,10-pentaene-14,16-dione. The structure of this dione product was proven by X-ray structural analysis.

Authors: A. G. Mikhailovskii, Z. G. Aliev, O. V. Surikova, and N. G. Efremova

English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (11), pp 1659-1664

http://link.springer.com/article/10.1007/s10593-013-1189-1

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Published

2013-08-23

Issue

No. 11 (2012)

Section

Original Papers