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Volumn 49, Issue 7, 2010, Pages 1306-1308

Sequential five-component construction of the cyclopenta [e]-[1,3]oxazine skeleton using stable 2-azetine derivatives

Author keywords

Alkynes; Azetines; Carbenes; Heterocycles; Regioselectivity

Indexed keywords

ACETYLIDES; AZETINES; CARBENES; CHEMICAL EQUATIONS; HETEROCYCLES; METHOXY; ONE-POT REACTION; REGIO-SELECTIVE; THREE-COMPONENT;

EID: 76349085437     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906357     Document Type: Article
Times cited : (30)

References (36)
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    • a) The isolation of dimethyl 1-ethyl-4-methyl-2-azetine-2,3-dicarboxylate in 9% yield has been reported; see: E. Winterfeldt, W. Krohn, Chem. Ber. 1969, 102, 2336-2345;
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    • Typical procedure involves the multistep synthesis of a suitable azetidine precursor, followed by elimination; a) see Ref. [2,3b,d,e]; b) Y. Dejaegher, S. Mangelinckx, N. De Kimpe, J. Org. Chem. 2002, 67, 2075-2081.
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    • Angew. Chem. Int. Ed. 2007, 46, 2610-2612;
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    • c) M. A. Sierra, Chem. Rev. 2000, 100, 3591-3637;
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    • The azetines 5 are stable when stored under nitrogen at 0-20°C.
    • The azetines 5 are stable when stored under nitrogen at 0-20°C.
  • 30
    • 76349122817 scopus 로고    scopus 로고
    • 3 = Ph) is employed, the expected azetine was not formed, but a [4+3] cyclization was observed wherein the phenylimine behaves as the 1-azadiene unit.
    • 3 = Ph) is employed, the expected azetine was not formed, but a [4+3] cyclization was observed wherein the phenylimine behaves as the 1-azadiene unit.
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    • 2 ≠ Fc) are used, undergo a [3+3] cyclization reaction to afford benzofurans; see Ref. [10c].
    • 2 ≠ Fc) are used, undergo a [3+3] cyclization reaction to afford benzofurans; see Ref. [10c].
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    • The reaction of the tungsten azetine complex 5g with paratolylacetylene formed a complex mixture rather than the expected cycloadduct 7b.
    • The reaction of the tungsten azetine complex 5g with paratolylacetylene formed a complex mixture rather than the expected cycloadduct 7b.
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    • For a sequence involving initial insertion of two alkyne units and carbon monoxide into a Fischer alkenyl carbene, followed by nucleophilic cyclization,see: F. Stein, M. Duetsch, R. Lackmann, M. Noltemeyer, A. de Meijere, Angew. Chem. 1991, 103, 1669-1671;
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    • b) it is well established that vinyl or allylammonium salts undergo the [3,3] rearrangement faster than their uncharged parent allylenamines; see: K. C. Majumdar, T. Bhattacharyya, B. Chattopadhyay, B. Sinha, Synthesis 2009, 2117-2142.
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    • Majumdar, K.C.1    Bhattacharyya, T.2    Chattopadhyay, B.3    Sinha, B.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.