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Volumn 74, Issue 9, 2009, Pages 3612-3615

Expedient and rapid synthesis of 1,2,3-triazolo[5,1-c]morpholines through palladium-copper catalysis

Author keywords

[No Author keywords available]

Indexed keywords

COPPER CATALYSIS; HIGH YIELD; MILD REACTION CONDITIONS; MORPHOLINES; ONE POT; RAPID SYNTHESIS; SHORT REACTION TIME;

EID: 66449120544     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900428j     Document Type: Article
Times cited : (37)

References (50)
  • 14
  • 32
    • 58149186450 scopus 로고    scopus 로고
    • Pericas and co-workers synthesized 1,2,3-triazolo-morpholines through conventional thermal cycloaddition approach. For details, see:(a) Oliva, A. I.; Christmann, U.; Font, D.; Cuevas, F.; Ballester, P.; Buschmann, H.; Torrens, A.; Yenes, S.; Pericas, M. A. Org. Lett. 2008, 10, 1617.
    • Pericas and co-workers synthesized 1,2,3-triazolo-morpholines through conventional thermal cycloaddition approach. For details, see:(a) Oliva, A. I.; Christmann, U.; Font, D.; Cuevas, F.; Ballester, P.; Buschmann, H.; Torrens, A.; Yenes, S.; Pericas, M. A. Org. Lett. 2008, 10, 1617.
  • 41
    • 66449109262 scopus 로고    scopus 로고
    • This perhaps arises from the fact that the axial N-C-Ph does not face any 1,3-diaxial interaction while it also avoids the 1,2-torsoinal strain with the neighboring N-N bond
    • This perhaps arises from the fact that the axial N-C-Ph does not face any 1,3-diaxial interaction while it also avoids the 1,2-torsoinal strain with the neighboring N-N bond.
  • 46
    • 0344944884 scopus 로고    scopus 로고
    • Soheili, A, Albaneze-Walker, J, Murry, J. A, Dormer, P. G, Hughes, D. L. Org. Lett. 2003, 5, 4191. We thank the referee for bringing ref 15a to our attention
    • (c) Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191. We thank the referee for bringing ref 15a to our attention.
  • 48
    • 66449117479 scopus 로고    scopus 로고
    • Intermediate species D (R ) R1 ) Ph, R2 ) H) was isolated, and several control experiments were carried out under various reaction conditions. However, expected cycloaddition was completed within 1 h (with 91% yield of desired product 3a), when the aforementioned intermediate D was heated in DMF at 100 °C in the presence of catalytic amount (10 mol %) of CuI only. Heating at 100 °C without CuI yielded the desired product 3a (54%) along with the recovery of unreacted intermediate D (41%) even after 14h.
    • Intermediate species D (R ) R1 ) Ph, R2 ) H) was isolated, and several control experiments were carried out under various reaction conditions. However, expected cycloaddition was completed within 1 h (with 91% yield of desired product 3a), when the aforementioned intermediate D was heated in DMF at 100 °C in the presence of catalytic amount (10 mol %) of CuI only. Heating at 100 °C without CuI yielded the desired product 3a (54%) along with the recovery of unreacted intermediate D (41%) even after 14h.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.