Ring transformation of 1,5‐diazabicyclo[3.1.0]hexanes under the action of arylketenes | Zendy

Shevtsov Alexander V. | Zendy; Kuznetsov Vladimir V. | Zendy; Kislukhin Alexander A. | Zendy; Petukhova Vera Yu. | Zendy; Strelenko Yu. A. | Zendy; Makhova Ni. | Zendy; Lyssenko Konstantin A. | Zendy

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Ring transformation of 1,5‐diazabicyclo[3.1.0]hexanes under the action of arylketenes

Author(s) -

Shevtsov Alexander V.,

Kuznetsov Vladimir V.,

Kislukhin Alexander A.,

Petukhova Vera Yu.,

Strelenko Yu. A.,

Makhova Ni.,

Lyssenko Konstantin A.

Publication year - 2006

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570430411

Subject(s) - chemistry , benzene , octane , toluene , bicyclic molecule , ring (chemistry) , hexane , ether , medicinal chemistry , aryl , nonane , stereochemistry , organic chemistry , alkyl

The reactions of 1,5‐diazabicyclo[3.1.0]hexanes 8 with arylketenes 1 have been studied in different conditions. The 1‐(arylacethyl)pyrazolidines 11 were obtained at −30 °C in ether and at 20 °C in benzene instead of the expected bicyclic systems 1,5‐diazabicyclo[3.2.1]octan‐6‐one 9 and 3‐aryl‐1,5‐diazabicyclo[3.3.0]octane‐2‐one 10 . The synthesis of two representatives of bicycles 10 ( 10a,b ) proceeded in the reaction of unsubstituted 1,5‐diazabicycle[3.1.0]hexane 8a , accordingly, with diphenylketene 1a in benzene at 20 °C and with 4‐chlorophenylketene 1b in toluene at 60‐110 °C. Mechanisms of the studied transformations were offered.

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