메뉴 건너뛰기




Volumn 65, Issue 6, 2000, Pages 1743-1749

A new route toward 4-substituted pyrazino[2,1-b]quinazoline-3,6-dione systems. Total synthesis of glyantrypine

Author keywords

[No Author keywords available]

Indexed keywords

FISCALIN B; FUMIQUINAZOLINE A; GLYANTRYPINE; N ACETYLARDEEMIN; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0034708411     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991626e     Document Type: Article
Times cited : (34)

References (38)
  • 20
    • 0028566539 scopus 로고
    • For some applications of this method to the synthesis of natural products, see: (b) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143 (total synthesis of N-acetylardeemin).
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 11143
    • Marsden, S.P.1    Depew, K.M.2    Danishefsky, S.J.3
  • 21
    • 0003153862 scopus 로고    scopus 로고
    • (c) He, F.; Snider, B. B. Synlett 1997, 483 (total synthesis of ent-fumiquinazoline G).
    • (1997) Synlett , pp. 483
    • He, F.1    Snider, B.B.2
  • 24
    • 0001003013 scopus 로고    scopus 로고
    • Related method: (a) Molina, P.; Alajarin, M.; Vidal, A.; Foces- Foces, M. C.; Hernández-Cano, F. Tetrahedron 1989, 45, 4263. (b) Villalgordo, J. M.; Obrecht, D.; Chucholowsky, A. Synlett 1998, 1405.
    • (1998) Synlett , pp. 1405
    • Villalgordo, J.M.1    Obrecht, D.2    Chucholowsky, A.3
  • 26
    • 0033582664 scopus 로고    scopus 로고
    • Treatment with piperidine to give an amidine carboxamide, followed by silica gel-induced cyclization to a 2-aminomethyl-3-carboxymethyl-3,4-dihydroquinazolin-4-one and then to the tricyclic system: He, F.; Snider, B. B. J. Org. Chem. 1999, 64, 1397. For an alternative method to achieve this cyclization, in the context of a synthesis of the alkaloid (-)-alantrypinone, see: Hart, D. J.; Magomedov, N. Tetrahedron Lett. 1999, 40, 5429.
    • (1999) J. Org. Chem. , vol.64 , pp. 1397
    • He, F.1    Snider, B.B.2
  • 27
    • 0033166696 scopus 로고    scopus 로고
    • Treatment with piperidine to give an amidine carboxamide, followed by silica gel-induced cyclization to a 2-aminomethyl-3- carboxymethyl-3,4-dihydroquinazolin-4-one and then to the tricyclic system: He, F.; Snider, B. B. J. Org. Chem. 1999, 64, 1397. For an alternative method to achieve this cyclization, in the context of a synthesis of the alkaloid (-)-alantrypinone, see: Hart, D. J.; Magomedov, N. Tetrahedron Lett. 1999, 40, 5429.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5429
    • Hart, D.J.1    Magomedov, N.2
  • 28
    • 0345623795 scopus 로고    scopus 로고
    • These intermediates were initially assigned as 2-aminomethyl-3-carboxymethyl-3,4-dihydroquinazolin-4-ones during the total synthesis of fumiquinazoline G and fiscalin B: Wang, H.; Ganesan, A. J. Org. Chem. 1998, 63, 2432.
    • (1998) J. Org. Chem. , vol.63 , pp. 2432
    • Wang, H.1    Ganesan, A.2
  • 29
    • 0000345938 scopus 로고
    • For the application of these conditions to the synthesis of oxazole derivatives from β-ketoamides, see: Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604.
    • (1993) J. Org. Chem. , vol.58 , pp. 3604
    • Wipf, P.1    Miller, C.P.2
  • 31
    • 0343851147 scopus 로고    scopus 로고
    • note
    • Use of higher pressures (4 atm) favors the cyclization of compounds 4 to the corresponding 2,5-piperazinediones.
  • 32
    • 0343415155 scopus 로고
    • Moody, C. J., Ed.; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., General Eds.; Pergamon Press: Elmsforg, NY, chapter 5.04
    • Bailey, P. D.; Collier, I. D.; Morgan, K. M. In Comprehensive Functional Group Chemistry; Moody, C. J., Ed.; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., General Eds.; Pergamon Press: Elmsforg, NY, 1995; chapter 5.04
    • (1995) Comprehensive Functional Group Chemistry
    • Bailey, P.D.1    Collier, I.D.2    Morgan, K.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.