Synthesis of Pyrroloquinones via a CAN Mediated Oxidative Free Radical Reaction of 1,3-Dicarbonyl Compounds with Aminoquinones

Table 1

General scheme for the oxidative free radical cyclization.

Compd no.	R	X	Y	Z
4a	Benzyl	CH3	OCH2CH3	I
4b	4-Nitrobenzyl	CH3	OCH2CH3	I
4c	4-Methoxybenzyl	CH3	OCH2CH3	I
4d	Benzyl	CH3	CH3	I
4e	4-Nitrobenzyl	CH3	CH3	I
4f	4-Methoxybenzyl	CH3	CH3	I
4g	Benzyl	CH3	C6H5	I
4h	4-Nitrobenzyl	CH3	C6H5	I
4i	4-Methoxybenzyl	CH3	C6H5	I
4j	Benzyl	CH3	N(CH3)2	I
4k	4-Nitrobenzyl	CH3	N(CH3)2	I
4l	4-Methoxybenzyl	CH3	N(CH3)2	I
5a	Benzyl	CH3	OCH2CH3	II
5b	4-Nitrobenzyl	CH3	OCH2CH3	II
5c	4-Methoxybenzyl	CH3	OCH2CH3	II
5d	Benzyl	CH3	CH3	II
5e	4-Nitrobenzyl	CH3	CH3	II
5f	4-Methoxybenzyl	CH3	CH3	II
5g	Benzyl	CH3	C6H5	II
5h	4-Nitrobenzyl	CH3	C6H5	II
5i	4-Methoxybenzyl	CH3	C6H5	II
5j	Benzyl	CH3	N(CH3)2	II
5k	4-Nitrobenzyl	CH3	N(CH3)2	II
5l	4-Methoxybenzyl	CH3	N(CH3)2	II