Pyrrolo benzoxazines

Thermal decomposition of l,2-dihydro-477-pyrrolo[2,l-r-][l,4]benzoxazine-l,2,4-triones 425 yielded 7-(2,4,6-trimethylbenzoyl)-8-[(2,4,6-trimethylphenoxycarbonyl)-6,10-dihydropyrido[2,l-r-][l,4]benzoxazine-6,10-dione by [4+2] cycloaddition of the initially formed ketene 426 and the subsequent rearrangement of 6,8,9,10-tetrahydropyrido[2,l-c][l,4]benzoxazine-6,8,10-trione 427 (Scheme 36) <1999RCB2131>. 

L-Proline also reacts with 2-hydroxy-6-methylacetophenones in boiling DMF to give racemic pyrrolo[2,l-h][l,3]benzoxazines 138 (79JOC4005). For the synthesis of pyrrolo[2,l-c][l,4]benzothiazepines 139, three different syntheses from L-Pro and 2-methylthiobenzoic acid or the disulfide of o-mercaptobenzoyl chloride have been described (88JHC1007). 

Antonelli, T., Tanganelli, S., Tomasini, M. C., Finetti, S., Trabace, L., Steardo, L., Sabino, V., Carratu, M. R., Cuomo, V., and Ferraro, L. (2004). Long-term effects on cortical glutamate release induced by prenatal exposure to the cannabinoid receptor agonist (7 )-(4-)-[2,3-dihydro-5-methyl-3-(4-morpholinyl-methyl)pyrrolo[l,2,3-de]-l,4-benzoxazin-6-yl]-l-naphthalenylmethanone An in vivo microdialysis study in the awake rat. Neuroscience 124, 367-375. 

A solid-supported carbonate reagent was used to initiate the formation of 2H-l,4-benzoxazin-2-ones 303 from P-nitroacrylate 301 and 2-aminophenol 302 (Scheme 7.72) [154]. This hetero-Michael addition/intramolecular transesteri-fication/elimination of HN03/[l,3]-proton shift domino reaction proceeded in moderate to excellent yields. In another study, a series of various functionalized pyrrolo[l,2-r]pyrazines 305 were made synthetically available through the reaction of vinyl azides 304 and lH-2-pyrrolecarbaldehyde (Scheme 7.73). The deprotonated pyrrole initially reacts in a Michael manner with the vinyl azides, with nitrogen as... 

Upon thermolysis, 3-aroyl-l,2-dihydro-4ff-pyrrolo[2,l-f][l,4]benzox-azine-l,2,4-triones 156a-f in inert aprotic solvents at 168—190 °C led to generation of 4-aroyl-3-aroyloxy-2-(2-oxo-2H-l,4-benzoxazin-3-yl)-lH,5H-pyrido-[2,l-c][l,4]-benzoxazine-l,5-diones 318a—f (Scheme 100)... 

C14H1eClNO, rac-cis-5-Chloro-2,3,3a,9-tetrahydro-6,8,9-trimethyl-lH-pyrrolo[2,l-b]benzoxazine, 45B, 406 Cl4H18CINO3S, 3 Chloromethylsulphonyl-p-methyl-a-morpholinostyrene (synclinal-5 and 5 ), 41B, 425... 

Ager IR, Barnes AC, Danswan GW, Hairsine PW, Kay DP, Kennewell PD, Matharu SS, Miller P, Robson P, Rowlands DA, Tully WR, Westwood R (1988) Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,l-c][l,4]benzoxazines, imidazo[l,2-tj] quinolines, imidazo[l,2-a]quinoxalines, imidazo[l,2-a]quinoxalinones, pyirolo[l,2-tj]quinox-alinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,l-f>]benzothiazoles. J Med Chem 31 (6) 1098-1115. doi 10.1021/jm00401a009... 

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