E. F. Sagitova, D. N. Tomilin, L. N. Sobenina, I. A. Ushakov, K. A. Apartsin, B. A. Trofimov, “Acyl-tetrahydroindolyl-capped 1,3-diynes in oxidative [4 + 2]-cycloaddition with benzylamine: a one-pot access to 2-acyl-6-phenyl-5-tetrahydroindolylpyridines”, Mendeleev Commun., 32:6 (2022), 729

Mendeleev Communications

RUS ENG

JOURNALS PEOPLE ORGANISATIONS CONFERENCES SEMINARS VIDEO LIBRARY PACKAGE AMSBIB

JavaScript is disabled in your browser. Please switch it on to enable full functionality of the website

	General information
	Latest issue
	Archive

	Search papers
	Search references

	RSS
	Latest issue
	Current issues
	Archive issues
	What is RSS

Mendeleev Commun.:
Year:
Volume:
Issue:
Page:
	Find

Personal entry:
Login:
Password:
	Save password
	Enter
	Forgotten password?
	Register

Mendeleev Communications, 2022, Volume 32, Issue 6, Pages 729–731
DOI: https://doi.org/10.1016/j.mencom.2022.11.007 (Mi mendc780)

This article is cited in 1 scientific paper (total in 1 paper)

Communications

Acyl-tetrahydroindolyl-capped 1,3-diynes in oxidative [4 + 2]-cycloaddition with benzylamine: a one-pot access to 2-acyl-6-phenyl-5-tetrahydroindolylpyridines

E. F. Sagitova^a, D. N. Tomilin^a, L. N. Sobenina^a, I. A. Ushakov^a, K. A. Apartsin^b, B. A. Trofimov^a

^a A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation
^b Biomedical Research and Technology Department of the Irkutsk Scientific Center, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation

Full-text PDF (172 kB) Citations (1) Supplementary materials

DOI: https://doi.org/10.1016/j.mencom.2022.11.007

Graphic abstract: Acyl-tetrahydroindolyl-capped 1,3-diynes in oxidative [4 + 2]-cycloaddition with benzylamine: a one-pot access to 2-acyl-6-phenyl-5-tetrahydroindolylpyridines

Abstract: 1-Acyl-4-tetrahydroindolyldiynes (available from cross-coupling of 4,5,6,7-tetrahydroindole with 1-acyl-4-bromo-1,3-diynes) undergo oxidative [4+2]-cycloaddition with benzylamine in KOH/DMSO or K3PO4/DMSO systems (80°C, 4 h) to afford 2-acyl-6-phenyl-5-tetrahydroindolyl-pyridines in ∼40% yields. Non-catalyzed reaction of the same reactants in boiling MeOH (4 h) or in DABCO/MeCN system (reflux, 1 h) gives 3-benzylaminoalk-2-en-4-ynones in ∼40% yields.

Keywords: tetrahydroindole, tetrahydroindolyldiyne, benzylamine, tetrahydroindolylpyridine, 3-benzylamino-2, 4-enyne.

Bibliographic databases:

Document Type: Article

Language: English

*Supplementary materials:*
		Supplementary_data_1.pdf	(1.4 Mb)

Citation: E. F. Sagitova, D. N. Tomilin, L. N. Sobenina, I. A. Ushakov, K. A. Apartsin, B. A. Trofimov, “Acyl-tetrahydroindolyl-capped 1,3-diynes in oxidative [4 + 2]-cycloaddition with benzylamine: a one-pot access to 2-acyl-6-phenyl-5-tetrahydroindolylpyridines”, Mendeleev Commun., 32:6 (2022), 729–731

Linking options:

https://www.mathnet.ru/eng/mendc780

https://www.mathnet.ru/eng/mendc/v32/i6/p729

This publication is cited in the following 1 articles:

Citing articles in Google Scholar: Russian citations, English citations
Related articles in Google Scholar: Russian articles, English articles

Registration to the website

Logotypes