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Synthesis of spiro[2 H ‐indole‐2,1′‐1 H ‐isoindole]‐3,3′‐diones, spiro[1 H ‐isobenzofuran‐1,2′‐2 H ‐indole]‐3,3′‐diones and spiro[benzofuran‐2,1′‐isobenzofuran]‐3,3′‐diones via transannular reactions of eight membered ring intermediates
Author(s) -
Bullington James L.,
Dodd John H.
Publication year - 1998
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570350223
Subject(s) - chemistry , isoindole , isobenzofuran , indole test , ninhydrin , benzofuran , furan , yield (engineering) , sodium periodate , medicinal chemistry , stereochemistry , organic chemistry , biochemistry , materials science , amino acid , metallurgy
Abstract An auto oxidation‐rearrangement product 4 was isolated from a high dilution reaction of ninhydrin with 3,4,5‐trimethoxyaniline in water. A general synthesis of this compound and its derivatives 4–6 was devised by oxidation of tetrahydroindeno[1,2‐ b ]indol‐10‐ones 1–3 with sodium periodate to give isoindolo[2,1‐ a ]‐indole‐6,11‐diones 4–6 in good yield. Compounds 4–6 can be easily transformed into spiro[1 H ‐isobenzofuran‐1,2′‐2 H ‐indole]‐3,3′‐diones 8–10 , spiro[2 H ‐indole‐2,1′‐1 H ‐isoindole]‐3,3′‐diones 11–13 and isoindole[1,2‐ a :2′,1′‐ b ]pyrimidine‐5,15‐diones 15, 16 in high yields. Analogous reactions were performed on 3‐amino‐5a, 10a‐dihydroxybenzo[ b ]indeno[2,1‐ d ]furan‐10‐one ( 17 ) to give a dibenzoxocintrione 18 , spiro‐[benzofuran‐2,1′‐isobenzofuran]‐3,3′‐dione 19 and an isoindol‐1‐one 20 .