A Di‐π‐Methane Rearrangement in the Photolysis of a 4‐Oxa‐steroidal α,β‐Unsaturated Enol‐lactone. Photochemical reactions VIII

Vallet, José Alberto; Boix, José; Bonet, J.-J.; Brianso, M. C.; Miravitlles, C.; Briansó, J. L.

doi:10.1002/hlca.19780610330

Cited by 8 publications

(1 citation statement)

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“…I7~-Hydroxy-4-aza-S~-androst-l-en-3-one (2). To a solution of 22 g of ammonium formate in 25 ml of HCOOH, 980 mg of 5 [9] were added. The mixture was refluxed for 24 h. The usual work-up with CHC13 yielded an oil that was dissolved in 50 ml of MeOH, treated with 50 ml of 4N aq.…”

Section: Experimental Partmentioning

confidence: 99%

Photochemical reactivity of α,β‐unsaturated δ‐lactams: Synthesis of seco‐steroids. Photochemical reactions. XIII [1]

Cánovas

Fonrodona

Bonet

et al. 1980

Helvetica Chimica Acta

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SummaryThe UV. irradiation of 17P-hydroxy-2-aza-4-androsten-3-one (l), N-methyl-17~-hydroxy-2-aza-4-androsten-3-one (3), 17~-hydroxy-4-aza-5~-androst-l -en-3-one (2) and N-methyl-17~-hydroxy-4-aza-5P-androst-l -en-3-one (4), gives rise to 1,lO-seco (from 1 and 3 ) and 5,lO-seco (from 2 and 4) steroids.Introduction. -Although in photochemical studies, lactams have received less attention than lactones and ketones, several examples can be found. Monocyclic [2] and bicyclic [3] compounds yield mainly fragmentation and sometimes [2b] dimerization products and the di-n-methane rearrangement of a lactam has been observed [4]. In the steroid field, several unsaturated lactams have been investigated. Enamidic lactams undergo photooxidation [5 J or photoisomerization [6], and A-homolactams yield mainly dimers [7]. Owing to the little work done on n,a-unsaturated 8-lactams, we decided to investigate the photolytic behaviour of lactams 1 , 2 , 3 and 4 (Scheme I).

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Section: Experimental Partmentioning

confidence: 99%