Simple and Condensed β-Lactams. Part 32. Base- and Acid-Catalyzed Ring Expansions of 3-Substituted 4-Acetylazetidin-2-ones and Related Compounds

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Title:Simple and Condensed β-Lactams. Part 32. Base- and Acid-Catalyzed Ring Expansions of 3-Substituted 4-Acetylazetidin-2-ones and Related Compounds
Creators:
Sápi, Attila
Fetter, József
Lempert, Károly
Kajtár-Peredy, Mária
Czira, Gábor
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 2, pp. 190-202
Uncontrolled Keywords:β-Lactams, Pyrazines, Azetidin-2-ones, Ring transformations

Abstract

On treatment with bases, the C3-C4 bonds of the 3-substituted 4-(1-iminoethyl)- or 4-acetylazetidin-2-ones <strong>8f</strong>, <strong>8g</strong> and <strong>8i</strong> are cleaved heterolytically to afford, depending on the nature of the 3-substituent, ring expansion or other products (<strong>14</strong>, <strong>19</strong> and <strong>27</strong>, respectively). Related compound <strong>8h</strong> undergoes a base-induced ring transformation to afford compound <strong>23</strong> only after oxidation to the stereoisomeric disulfanes <strong>20</strong>. Compound <strong>8d</strong>, when treated with HCl, undergoes a ring transformation to pyrrolidin-2-one <strong>32</strong>. <p>

Title:Simple and Condensed β-Lactams. Part 32. Base- and Acid-Catalyzed Ring Expansions of 3-Substituted 4-Acetylazetidin-2-ones and Related Compounds
Creators:
Sápi, Attila
Fetter, József
Lempert, Károly
Kajtár-Peredy, Mária
Czira, Gábor
Uncontrolled Keywords:β-Lactams, Pyrazines, Azetidin-2-ones, Ring transformations
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:64
Number:2
Page Range:pp. 190-202
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990190UNSPECIFIED
ID Code:1469
Item Type:Article
Deposited On:06 Feb 2009 17:09
Last Modified:06 Feb 2009 16:09

Citation

Sápi, Attila; Fetter, József; Lempert, Károly; Kajtár-Peredy, Mária; Czira, Gábor (1999) Simple and Condensed β-Lactams. Part 32. Base- and Acid-Catalyzed Ring Expansions of 3-Substituted 4-Acetylazetidin-2-ones and Related Compounds. Collection of Czechoslovak Chemical Communications, 64 (2). pp. 190-202. ISSN 0010-0765

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