TY - JOUR
T1 - Structure determination of the products from the acid-catalyzed condensation of indole with acetone
AU - Noland, Wayland E
AU - Konkel, Michael J.
AU - Konkel, Lisa M.C.
AU - Pearce, Bradley C.
AU - Barnes, Charles L.
AU - Schlemper, Elmer O.
PY - 1996/1/26
Y1 - 1996/1/26
N2 - Four of the previously reported compounds obtained from the acid-catalyzed condensation of indole with acetone are now assigned the following structures: cis-4,4a,9,9a-tetrahydro-2-(1H-indol-3-yl)-4,4-dimethyl-3H-carbazole (2a), 1,1',4,4'-tetrahydro-1,1,1',1'-tetramethyl-3,3'(2H,2'H)-spirobi[cyclop ent[b]indole] (4), 4,4a-dihydro-2-(3-1H-indolyl)-4,4-dimethyl-3H-carbazol-4a-ol (7), and 5-(2-aminophenyl)-1,3,4,5-tetrahydro-1,1,4,4-tetramethylcyclopent[kl]a cridine (8). The structure of the novel rearrangement product 8 was solved by an X-ray crystal structure determination. The two previously reported autoxidation products of 4 are now assigned the following structures: 1,3',4,4'-tetrahydro-1,1,4',4'-tetramethyl-cis-dispiro[cyclopent[b]ind ole-3(2H),2'(5'H)-furan-5',3''-[3H]-indol]2''(1''H)-one (5) and 1,4-dihydro-1,1,5',5'-tetramethylspiro[cyclopent[b]indole-3(2H),3'(4'H )-1-benzazocine]-2'(1'H),6'(5'H)-dione (6).
AB - Four of the previously reported compounds obtained from the acid-catalyzed condensation of indole with acetone are now assigned the following structures: cis-4,4a,9,9a-tetrahydro-2-(1H-indol-3-yl)-4,4-dimethyl-3H-carbazole (2a), 1,1',4,4'-tetrahydro-1,1,1',1'-tetramethyl-3,3'(2H,2'H)-spirobi[cyclop ent[b]indole] (4), 4,4a-dihydro-2-(3-1H-indolyl)-4,4-dimethyl-3H-carbazol-4a-ol (7), and 5-(2-aminophenyl)-1,3,4,5-tetrahydro-1,1,4,4-tetramethylcyclopent[kl]a cridine (8). The structure of the novel rearrangement product 8 was solved by an X-ray crystal structure determination. The two previously reported autoxidation products of 4 are now assigned the following structures: 1,3',4,4'-tetrahydro-1,1,4',4'-tetramethyl-cis-dispiro[cyclopent[b]ind ole-3(2H),2'(5'H)-furan-5',3''-[3H]-indol]2''(1''H)-one (5) and 1,4-dihydro-1,1,5',5'-tetramethylspiro[cyclopent[b]indole-3(2H),3'(4'H )-1-benzazocine]-2'(1'H),6'(5'H)-dione (6).
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U2 - 10.1021/jo951596p
DO - 10.1021/jo951596p
M3 - Article
AN - SCOPUS:0030052115
SN - 0022-3263
VL - 61
SP - 451
EP - 454
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -