A novel synthesis of 2-(2-quinoxalino)-3,5-diarylfurans

Tetrahedron Letters

Volumn 39, Issue 44, 1998, Pages 8017-8020

  Duffy, Kevin J ^a   Haltiwanger, R Curtius ^a   Huang, Yifang ^a   Konialian Beck, Arda ^a   Luengo, Juan I ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Cyclization; Furans; Oxidation; Quinoxalines; X ray crystal structure

Indexed keywords

2 (2 QUINOXALINO) 3,5 DIARYLFURAN; FURAN DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; MASS SPECTROMETRY; OXIDATION; SYNTHESIS; X RAY ANALYSIS;

EID: 0032578823     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01790-0     Document Type: Article

References (13)

1. 1 For a thorough review see Comp. Heterocylc. Chem., Volume 4, Part 3, Katritzky AK and Rees CW. eds., 1984. Pergamon Press.
2. 2 Paal C. Ber., 1884, 17, 2756.
3. 3 Blomquist AT and Stevenson HB. J. Amer. Chem. Soc., 1934, 56, 146.
4. 4 Nishiyama H; Sasaki M and Itoh K. Chem. Lett. 1981, 1363.
5. 5 Backer HJ and Stevens W. Rec. Trav. Chim. Pays-Bas, 1940, 59, 423.
6. 6 a. Cazaux L; Faher M; Picard C and Tisnes P. Can. J. Chem., 1993, 71, 2007;
7. b. Badr MZA and El-Naggar GM. Bull. Chem. Soc. Jpn., 1984, 57, 1653;
8. c. Ahmad AR, Mehta LK and Parrick J. Tetrahedron, 1995, 51, 12899.
9. 7 The cyclization reactions described in this letter are generally very clean (TLC analysis), but the yield of isolated products are only moderate (usually in the range of 25-40%). It is not yet established whether this low yield is due to a problem with isolation and/or with unidentified side-reactions.
10. 8 Treatment of 9 with NaH followed by MeI affords a 9:1 mixture of N/O-methylated products.
11. 9 4-Nitroacetophenone failed to give any Michael addition product with 12 under a variety of base-catalyzed conditions (NaH, LDA, n-BuLi, solvents, temperatures).
12. 2Br) calcd: C, 65,66; H, 3.75; N, 6.13 found: C, 65.44; H, 3.82; N, 5.93.
13. max = 0.00) to values of the conventional crystallographic residuals R = 0.069 for observed data (2527 data; I>2σ(I)) and R = 0.111 (wR2 = 0.236) for all data. The atomic co-ordinates for this work are available on request from the Director of the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW. Any request should be accompanied by the full literature citation for this communication.