Synthesis of Hexahydropyridazines by [4 + 2] Cycloaddition of Donor–Acceptor Cyclobutanes and cis-Diazenes

Synthesis of Hexahydropyridazines by [4 + 2] Cycloaddition of Donor–Acceptor Cyclobutanes and cis-Diazenes

The GaCl3-catalyzed [4 + 2] cycloaddition between alkoxy- and aryl-activated donor–acceptor cyclobutane diesters and cis-diazene 1a (4-phenyl-1,2,4-triazoline-3,5-dione, PTAD) is disclosed. The reaction provides hexahydropyridazine derivatives as single diastereomers in good to excellent yields in m...

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Veröffentlicht in:Organic letters 2020-04, Vol.22 (8), p.3140-3144
Hauptverfasser: Wu, Jackie, Winiarz, Paul, Patel, Dhwanish, de Jong, Johanna, Tong, David, Chidley, Tristan, Vemula, Naresh, Pagenkopf, Brian L
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container_end_page 3144
container_issue 8
container_start_page 3140
container_title Organic letters
container_volume 22
creator Wu, Jackie
Winiarz, Paul
Patel, Dhwanish
de Jong, Johanna
Tong, David
Chidley, Tristan
Vemula, Naresh
Pagenkopf, Brian L
description The GaCl3-catalyzed [4 + 2] cycloaddition between alkoxy- and aryl-activated donor–acceptor cyclobutane diesters and cis-diazene 1a (4-phenyl-1,2,4-triazoline-3,5-dione, PTAD) is disclosed. The reaction provides hexahydropyridazine derivatives as single diastereomers in good to excellent yields in most cases. The structural assignment of the cycloadduct 3b was unambiguously established by single-crystal X-ray diffraction.
doi_str_mv 10.1021/acs.orglett.0c00896
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title Synthesis of Hexahydropyridazines by [4 + 2] Cycloaddition of Donor–Acceptor Cyclobutanes and cis-Diazenes
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