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Synlett 2020; 31(07): 672-676
DOI: 10.1055/s-0039-1691586
letter
© Georg Thieme Verlag Stuttgart · New York

Unusual Transformations of Cyclic Allenes with an Enamine Moiety into Complex Frameworks

Alexander A. Titov  ∗
a   Organic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow 117198, Russian Federation   eMail: titov-aa@rudn.ru
,
Maxim S. Kobzev
a   Organic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow 117198, Russian Federation   eMail: titov-aa@rudn.ru
,
Tatiana N. Borisova
a   Organic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow 117198, Russian Federation   eMail: titov-aa@rudn.ru
,
Elena A. Sorokina
a   Organic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow 117198, Russian Federation   eMail: titov-aa@rudn.ru
,
Erik Van der Eycken
a   Organic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow 117198, Russian Federation   eMail: titov-aa@rudn.ru
b   Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven 3001, Belgium
,
Alexey V. Varlamov
a   Organic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow 117198, Russian Federation   eMail: titov-aa@rudn.ru
,
Leonid G. Voskressensky
a   Organic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow 117198, Russian Federation   eMail: titov-aa@rudn.ru
› InstitutsangabenThe publication has been prepared with the support of the ‘RUDN University Program 5-100’ and by the Russian Foundation for Basic Research (projects No. 18-33-00526, 17-03-00605).
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Publikationsverlauf

Received: 05. Dezember 2019

Accepted after revision: 08. Januar 2020

Publikationsdatum:
04. Februar 2020 (online)

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Abstract

The thermolysis reactions of benzoazacyclodecatrienes under microwave irradiation conditions in toluene at 150 °C afforded complex azabenzo[a]cyclopropa[cd]azulene and (epiminomethano)cyclopenta[a]indene frameworks. Cyclopropanes were established as intermediates of the ultimate thermolysis products.

Key words

thermal transformation - azacyclic allene - cyclopropanes - epiminomethanocyclopentaindenes - microwave-assisted reaction - polyheterocyclic compounds

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1691586.
  • Supporting Information

Primary Data

    for this article are available online at https://doi.org/10.1055/s-0039-1691586 and can be cited using the following DOI: 10.4125/pd0114th.

  • Primary Data
 

  • References and Notes

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  • 15 General Procedure A A solution of the appropriate allene derivative (0.68 mmol) in dry toluene (6.0 mL) was placed in a microwave reactor and heated at 150 °C for 30 min while the progress of the reaction was monitored by TLC [EtOAc–hexane, 1:1 (4a and 4c); EtOAc–hexane, 1:2 (4b, 4d, and 4e)]. The solvent was evaporated in vacuo. Products 7a–c, 7e, and 8a–e were isolated by chromatography on silica gel; compounds 7a and 7c, 7b and 8b, 7e, 8a, 8c, and 8e were eluted with EtOAc–hexane (1:3, 1:5, 1:12, 1:2, 1:1, and 1:10, respectively).
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