2010
DOI: 10.3998/ark.5550190.0011.926
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A facial synthesis of quinazolino[1,4]benzodiazepine alkaloids via reductive N-heterocyclization of N-(2-nitrobenzoyl)amides: total synthesis of asperlicin C, circumdatin H, and its analogues

Abstract: A facile and short synthesis of a series of quinazolino [1,4]benzodiazepine alkaloids, including asperlicin C, circumdatin H and some analogues, is reported utilizing coupling of readily available [1,4]benzodiazepine with 2-nitrobenzoyl chlorides, followed by a reductive Nheterocyclization.

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Cited by 14 publications
(5 citation statements)
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“…Quinazolinone 4r deriving from challenging hindered o -toluidine was obtained in 42% yield, while with n -pentylamine the corresponding product 4s was prepared in 59% yield. By using l -leucine methyl ester as amine, instead of the desired product, benzo­[1,4]­diazepine-2,5-dione 6 was obtained in a not-optimized 32% yield . This result demonstrates that anthranilic acids in combination with T3P are a practical synthetic equivalent of isatoic anhydride V , known to condense with α-amino acids for the preparation of benzo­[1,4]­diazepine-2,5-diones. With regards to the acid partner, variation was achieved by using commercially available chlorodifluoroacetic acid and pentafluoropropionic acid as examples, allowing for the preparation of the corresponding quinazolinones 4t , u in reasonable yields.…”
Section: Resultsmentioning
confidence: 95%
“…Quinazolinone 4r deriving from challenging hindered o -toluidine was obtained in 42% yield, while with n -pentylamine the corresponding product 4s was prepared in 59% yield. By using l -leucine methyl ester as amine, instead of the desired product, benzo­[1,4]­diazepine-2,5-dione 6 was obtained in a not-optimized 32% yield . This result demonstrates that anthranilic acids in combination with T3P are a practical synthetic equivalent of isatoic anhydride V , known to condense with α-amino acids for the preparation of benzo­[1,4]­diazepine-2,5-diones. With regards to the acid partner, variation was achieved by using commercially available chlorodifluoroacetic acid and pentafluoropropionic acid as examples, allowing for the preparation of the corresponding quinazolinones 4t , u in reasonable yields.…”
Section: Resultsmentioning
confidence: 95%
“…Upon treatment with tributylphosphine, cyclization occurred to deliver the natural product. Alternatively, Al‐Said et al 210 reacted 224 with acid chloride 227 (Scheme 24B). The reduction of the nitro group under classic hydrogenation conditions occurred with concomitant dehydration to deliver circumdatin H ( 56 ).…”
Section: Total Synthesesmentioning
confidence: 99%
“…In terms of synthetic raw materials, they are benzoic acid derivatives with o-NH 2 or other substituents [22][23][24][25][26][27][28] and isatin anhydride. [29][30][31] In general, the method of gaining quinazolinone derivatives from benzoic acid derivatives with o-NH 2 or other substituents is facile.…”
mentioning
confidence: 99%