IMDAV reaction between phenylmaleic anhydride and thienyl(furyl)allylamines: synthesis and molecular structure of (3aSR,4RS,4aRS,7aSR)-5-oxothieno- and (3aSR,4SR,4aRS,7aSR)-5-oxofuro[2,3-f]isoindole-4-carboxylic acids

Abstract

To establish the scope and limitations of the IMDAV reaction by elucidation of its regio- and stereoselectivity, the products of the reaction between phenyl­maleic anhydride and thien­yl(fur­yl)allyl­amines were studied by X-ray diffraction

Application of the Intramolecular Diels–Alder Vinylarenе (IMDAV) Approach for the Synthesis of Thieno[2,3-f]isoindoles

“…Calcd for C 17 H 14 ClNO 3 S: C,58.70;H,4.06;N,4.03;S,9.22. Found: C,58.49;H,4.13;N,4.25;S,9.09. (4RS,4aRS,7aSR)-6-(4-Bromophenyl)-5-oxo-4a,5,6,7,7a,8-hexahydro-4H-thieno[2,3-f…”

“…(4RS,4aRS,7aSR)-6-(4-Methylphenyl)-5-oxo-4a,5,6,7,7a,8-hexahydro-4H-thieno[2,3-f 2, 172.1, 137.4, 136.7, 132.6, 131.8, 129.0, 127.4, 123.7, 118.9, 51.4, 47.3, 40.0, 32.6, 28.0, 20.4 H,5.23;N,4.28;S,9.79. Found: C,65.82;H,5.16;N,4.41;S,9. 3, 172.7, 139.2, 137.2, 132.2, 129.1, 128.1, 127.9, 124.4, 120.9, 51.9, 47.8, 40.5, 32.3, 28. Anal. Calcd for C 17 H 14 ClNO 3 S: C,58.70;H,4.06;N,4.03;S,9.22.…”

“…Calcd for C 18 H 17 NO 3 S: C,66.03;H,5.23;N,4.28;S,9.79. Found: C,65.91;H,5.30;N,4.34;S,9.64. (4RS,4aRS,7aSR)-2-Ethyl-5-oxo-6-phenyl-4a,5,6,7,7a,8-hexahydro-4H-thieno[2,3-f 7.34 (dd,J = 7.4,8.7 Hz,2 H,3,5-H Ar ), 7.08 (t, J = 7.4 Hz, 1 H, 4-H Ar ), 6.70 (s, 1 H, 3-H), 3.97 (dd, J = 7.4, 9.1 Hz, 1 H, 7-H A ), 3.85 (dd, J = 1.2, 5.2 Hz, 1 H, 4-H), 3.65 (dd, J = 9.1, 9.9 Hz, 1 H, 7-H B ), 3.10-3.02 (m, 1 H, 7a-H), 2.97 (dd, J = 5.2, 15.3 Hz, 1 H, 4a-H), 2.76 (dd, J = 5.4, 12.4 Hz, 1 H, 8-H A ), 2.71 (q, J = 7.4 Hz, 2 H, CH 2 ), 2.66 (dd, J = 12.4, 14.5 Hz, 1 H, 8-H B ), 1.17 (t, J = 7.4 Hz, 3 H, CH 3 ).…”

“…8, 145.0, 140.2, 134.5, 131.4, 129.3, 124.3, 119.5, 55.3, 52.0, 47.8, 40.6, 33.0, 28.5, 23.3, 16.3 S: C,66.84;H,5.61;N,4.10;S,9.39. Found: C,66.98;H,5.47;N,4.31;S,9.48. (4RS,4aRS,7aSR)-5-Oxo-6-phenyl-2-propyl-4a,5,6,7,7a,8-hexahydro-4H-thieno[2,3-f 1, 172.8, 143.0, 140.4, 134.6, 131.5, 129.2, 125.1, 124.1, 119.4, 51.9, 47.8, 40.6, 33.0, 32.0, 28.6, 24.9, 14. 6, 172.5, 141.4, 140.2, 138.1, 136.9, 136.6, 132.2, 130.2 (2 C), 129.2, 128.0, 125.9, 124.2, 121.7, 119.4, 51.8, 48.4, 40.5, 32.2, 29.0, 20 Anal.…”

“…Calcd for C 18 H 17 NO 3 S: C,66.03;H,5.23;N,4.28;S,9.79. Found: C,66.17;H,5.31;N,4.19;S,9.62. (3aSR,4RS,4aRS,7aRS)-4-Methyl-6-(4-methylphenyl)-5-oxo-4,4a,5,6,7,7a-hexahydro-3aH-thieno[2,3-f]isoindole-4-carboxylic Acid (7c) Colorless powder; yield: 0.042 g (31%); mp 147-149 °C (dec.).…”