1991
DOI: 10.1002/jhet.5570280601
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Abstract: The 13C nmr spectra of 2‐ or 3‐monosubstituted furo[2,3‐b]‐ 1a‐1j, furo[3,2‐b]‐ 2a‐2j, furo[2,3‐c]‐ 3a‐3j and furo[3,2‐c]pyridine derivatives 4a‐4j are reported. Effects by change in annelation and substituent effects on 13C chemical shifts and carbon‐proton coupling constants are discussed. The spectra of benzo[b]furan derivatives 5a‐5j having the corresponding substituent are also reported for comparison.

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Cited by 17 publications
(3 citation statements)
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“…A solution of furopyridine 1a-d [2][3][4][5] (1.0 mmol) in dry ether (ca. 3 ml) was added to liquid ammonia (10 ml), and sodium metal (3.0 or 1.8 mmol) was then added to the solution, and the mixture was stirred for 30 minutes.…”
Section: General Procedures For Birch Reduction Of 1a-dmentioning
confidence: 99%
“…A solution of furopyridine 1a-d [2][3][4][5] (1.0 mmol) in dry ether (ca. 3 ml) was added to liquid ammonia (10 ml), and sodium metal (3.0 or 1.8 mmol) was then added to the solution, and the mixture was stirred for 30 minutes.…”
Section: General Procedures For Birch Reduction Of 1a-dmentioning
confidence: 99%
“…N - (2( R )-Hydroxy-1( S )-indanyl)-2( R )-phenylmethyl-4( S )-hydroxy-5-(1-(4-(2-(6-methylfuro[3 ,2- c ]pyridyl)methyl)-2( S )- N ‘ -( tert -butylcarboxamido)piperazinyl))pentanamide (31). The preparation of 2-formyl-6-methylfuro[3,2- c ]pyridine followed in analogous fashion from the synthesis of 2-formylfuro[3,2- c ]pyridine, using β-(3-furyl)methacrylic acid in place of β-(3-furyl)acrylic acid. Starting from 2-formyl-6-methylfuro[3,2- c ]pyridine and amine 2 and following the procedure outlined in method A, compound 31 was prepared as a white solid in 78% yield: mp 101−110 °C; TLC (MeOH:CHCl 3 saturated with NH 3 :CH 2 Cl 2 , 10:30:60) R f = 0.36; 1 H NMR (400 MHz, CDCl 3 ) δ 1.36 (s, 9H), 1.49−1.58 (m, 1H), 1.91−2.01 (m, 1H), 2.25 (br s, 1H), 2.43−2.50 (m, 2H), 2.52−2.62 (m, 4H), 2.64 (s, 3H), 2.70−3.03 (m, 7H), 3.09 (br s, 1H), 3.61 (d, J = 14.1 Hz, 1H), 3.66 (d, J = 14.1 Hz, 1H), 3.78−3.86 (m, 1H), 4.14 (br s, 1H), 4.28 (dd, J = 4.9, 3.9 Hz, 1H), 5.26 (dd, J = 8.4, and 4.9 Hz, 1H), 6.43 (d, J = 8.6 Hz, 1H), 6.62 (s, 1H), 7.05−7.29 (m, 10H), 7.92 (br s,1H), 8.70 (s, 1H); HRMS (FAB-POSI; M + 1) calcd 668.3811, found 688.3803.…”
Section: Methodsmentioning
confidence: 99%
“…Assigned 13 C NMR shifts (DMSO- d 6 ) of the quinuclidin-2-ene (Q2−Q8) and benzofuran (C2−C7a) carbons of the 5- and 7-substituted quinuclidin-2-ene derivatives. The 13 C NMR spectra were assigned by using standard shift theory, comparisons with selected benzofuran derivatives, and 1 H− 13 C heteronuclear NMR correlation experiments (2 pages) . Ordering information is given on any current masthead page.…”
Section: Supporting Information Availablementioning
confidence: 99%