Synthesis and nucleophilic properties of 1-(2-methoxyethyl) and 1-(2-phenoxyethyl)-3,3-dialkyl-3,4-dihydroisoquinolines

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

The Ritter reaction of dialkyl benzyl carbinols with 3-methoxy- and 3-phenoxypropanenitriles afforded the corresponding 1-(2-methoxyethyl)- and 1-(2-phenoxyethyl)-3,3-dialkyl-3,4-dihydroisoquinolines. Likewise, benzo[f]isoquinoline derivatives were synthesized from 2-methyl-3-(naphthalen-1-yl)propan-2-ol. The obtained compounds were shown to have the imine structure, but they exhibited enamine properties. In particular, their reactions with oxalyl chloride resulted in pyrrole annulation.

About the authors

A. G. Mikhailovskii

Perm State Pharmaceutical Academy

Author for correspondence.
Email: neorghim@pfa.ru
ORCID iD: 0000-0002-5104-4877
Russian Federation, ul. Polevaya, 2, Perm, 614990

A. S. Yusov

Perm State Pharmaceutical Academy

Email: neorghim@pfa.ru
ORCID iD: 0000-0003-4059-2613
Russian Federation, ul. Polevaya, 2, Perm, 614990

N. N. Pershina

Perm State Pharmaceutical Academy

Email: neorghim@pfa.ru
ORCID iD: 0000-0002-1422-2902
Russian Federation, ul. Polevaya, 2, Perm, 614990

References

  1. Шкляев В.С., Александров Б.Б., Леготкина Г.И., Вахрин М.И., Гаврилов М.С., Михайловский А.Г. ХГС. 1983, 11, 1560. [Shklyaev V.S., Aleksandrov B.B., Legotkina G.I., Vakhrin M.I., Gavrilov M.S., Mikhailovskii A.G., Chem. Heterocycl. Compd. 1983, 19, 1242.] doi: 10.1007/BF00515370
  2. Шкляев В.С., Александров Б.Б., Михайловский А.Г., Вахрин М.И. ХГС. 1989, 9 1239–1242.[Shklyaev V.S., Aleksandrov B.B., Mikhailovskii A.G., Vakhrin M.I., Chem. Heterocycl. Compd. 1989, 25, 1038–1041.] doi: 10.1007/BF00487305
  3. Шкляев В.С., Александров Б.Б., Гаврилов М.С., Михайловский А.Г., Вахрин М.И. ХГС. 1988, 8, 939–942. [Shklyaev V.S., Aleksandrov B.B., Gavrilov M.S., Mikhailovskii A.G., Vakhrin M.I., Chem. Heterocycl. Compd. 1988, 24, 772–775.] doi: 10.1007/BF00633173
  4. Полыгалова Н.Н., Михайловский А.Г., Вахрин М.И. ХГС. 2006, 9, 1382–1387. [Polygalova N.N., Mikhailovskii A.G., Vakhrin M.I. Chem. Heterocycl. Compd. 2006, 42, 1200–1204.] doi: 10.1007/s10593–006–0226–8
  5. Халтурина В.В., Шкляев Ю.В., Алиев З.Г., Масливец А.Н. ЖОрХ. 2009, 45, 1587–1588. [Khalturina V.V., Shklyaev Yu. V., Aliev Z.G., Maslivets A.N. Russ. J. Org. Chem. 2009, 45, 1576–1577.] doi: 10.1134/s1070428009100297
  6. Халтурина В.В., Шкляев Ю.В., Махмудов Р.Р., Масливец А.Н. Хим.-фарм. ж. 2010, 44, 7–9. [Khalturina V.V., Shklyaev Yu. V., Mahmudov R.R., Maslivets A.N. Pharm. Chem. J. 2010, 44, 594–596.] doi: 10.1007/s11094–011–0524-Z
  7. Коновалова В.В., Харитонова А.В., Шкляев Ю.В., Масливец А.Н. ЖОрХ. 2015, 51, 1597–1602. [Konovalova V.V., Kharitonova A.V., Shklyaev Yu.V., Maslivets A.N. Russ. J. Org. Chem. 2015, 51, 1566–1571.] doi: 10.1134/s1070428015110081
  8. Михайловский А.Г., Корчагин Д.В., Юсов А.С., Гашкова О.В. ХГС. 2016, 52, 852–854. [Mikhailovskii A.G., Korchagin D.V., Yusov A.S., Gashkova O.V. Chem. Heterocycl. Compd. 2016, 52, 852–854.] doi: 10.1007/s10593–016–1977–5
  9. Михайловский А.Г., Погорелова Е.С., Першина Н.Н., Махмудов Р.Р., Новикова В.В. Хим.-фарм. ж. 2019, 53, 25–29 [Mikhailovskii A.G., Pogorelova E.S., Mahmudov R.R., Novikova V.V. Pharm. Chem. J. 2019, 53, 1013–1017.] doi: 10.1007/s11094–020–02115-Z
  10. Дормидонтов М.Ю., Сыропятов Б.Я., Даутова Р.З., Александров Б.Б., Шкляев В.С., Вахрин М.И., Михайловский А.Г. Хим.-фарм. ж. 1990, 24, 22–24. [Dormidontov M. Yu., Syropyatov B. Ya., Dautova R.Z., Aleksandrov B.B., Shklyaev V.S., Vakhrin M.I., Mikhailovskii A.G. Pharm. Chem. J. 1990, 24, 882–885.] doi: 10.1007/BF00766580
  11. Терентьев А.П., Кост А.Н. Реакции и методы исследования органических соединений. М.: Госхимиздат. 1952, 2, 47–208.
  12. Дарьин Д.В., Лобанов П.С. Усп. хим. 2015, 84, 601–633. [Dar’in D.V., Lobanov P.S. Russ. Chem. Rev. 2015, 84, 601–633.] doi: 10.1070/RCR4528

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2024 Russian Academy of Sciences