Synthesis p. 795 - 800 (1995)
Update date:2022-08-02
Topics:
Merz
Schropp
Dotterl
A five-step general synthesis of 3,4-dialkoxypyrroles 7c-f is described starting with the condensation of dimethyl N-benzyliminodiacetate (1 b) and diethyl oxalate to give dimethyl 1-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (2b), which is bis-O-alkylated to the corresponding 3,4-diethers 3c-g. Pyrrole N-benzyl cleavage followed by ester hydrolysis and decarboxylation leads to 7c-f in 10-50% overall yield. Pyrroles 7c-f react with formaldehyde or benzaldehydes to give meso-H- (8a-d) or meso-tetraaryloctaalkoxyporphyrins 9a-g in moderate yields.
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Doi:10.3762/bjoc.16.65
(2020)Doi:10.1007/s10593-009-0355-y
(2009)Doi:10.1021/ja01068a026
(1964)Doi:10.1021/ja01187a010
(1948)Doi:10.1021/ol062589y
(2006)Doi:10.1016/S0040-4020(01)99320-2
(1984)