Diazepinones, synthesis

Pyrazolo[3,4-d][l,2]diazepines synthesis, 7, 597 Pyrazolop, 4- 6][ 1,4]diazepines synthesis, 5, 272 Pyrazolo[l, 4]diazepinones as anticonvulsant, 1, 170 Pyrazolo[2,3-e]diazepinones synthesis, 5, 272 1 H-Pyrazolo[l,5-6]imidazoles synthesis, 6, 992 Pyrazolo[2,3-a]imidazoles biological activity, 6, 1024 Pyrazolo[2,3-c]imidazoles reactions, 6, 1041 synthesis, 6, 1047 Pyrazolo[2,3-imidazoles synthesis, 6, 991 Pyrazolo[3,2- njisoquinolines synthesis, 5, 339 Pyrazolop, 4-c]isoquinolines synthesis, 5, 273 Pyrazolonaphthyri dines synthesis, 5, 339 Pyrazolone, diazophotolysis, 5, 252 Pyrazolone, 4,4-dihalo-rearrangements, 5, 250 Pyrazolone, ethoxy-hydrazinolysis, 5, 253 Pyrazolone, 4-halo-... 

Thieno[ 1,2,3]diazaborines, dihydro-bromination, 1, 656 deuteration, 1, 658 iodination, 1, 656 nitration, 1, 656 nucleophilic substitution copper-promoted, 1, 658 Thienodiazepines synthesis, 7, 595 Thieno[ 1,2]diazepines synthesis, 7, 598 Thieno[2,3-d][l, 2]diazepines synthesis, 4, 749 Thieno[3,2-d][l,2]diazepines synthesis, 4, 749 Thieno[ 1,3]diazepines synthesis, 7, 607 Thieno[ 1,4]diazepinones as anticonvulsants, 1, 170 Thieno[3,4-d][l,3]dioxol-2-one, 4,6-diphenyl-... 

The synthesis of the tetracyclic pyrido[3,2- >]furo [3,2-6Jbenzo[l,4j-diazepinone (47) starting with 2-cyano-3-hydroxypyridine (42) and 3-... 

A similar diazepinone formation was performed for the synthesis of 53. In this case, however, the cyclization was performed via the formation of a mixed anhydride (Equation 5) <2001EJM407>. 

A one-pot cascade reductive amination, conjugate addition and lactamisation of keto acrylate 112 afforded fused piperidinodiazepinone 113 in good yield <07T7187> while lactamisation was the final step in the synthesis of tetracyclic diazepinone natural products sclerotigenin and (-)-circumdatin-F <07TL3243>. 

In the synthesis of the Nevirapine ring system [161], q clization of chloro-amine 392 (Scheme 127) afforded diazepinone derivatives 395 and 397 along with chloro-amide 396. Products 396 and 397 were formed via spirocyclic intermediate 393. The relative amounts of 395, 396 and 397 could be subjected... 

Purines have also been obtained by transformations of appropriate pteridines (75CPB2678,73CB3203). Also the 6-azapteridine (363) on reduction produced 8-substituted theophylline (Scheme 154) (69MI40900). Similarly the 7-azapteridine (364) with hot formamide afforded 8-phenyltheophylline (Scheme 154) (76H(4)749), and the diazepinone (365) with alkoxide also produced the 9-(2-propenyl)purine (366) by what is ultimately a Traube synthesis (Scheme 155) (70JHC1029). 

Novel non-nucleoside inhibitors of HIV-1 reverse transcriptase, dipyrido[2,3-/)]diazepinones, were prepared by J.R. Proudfoot and co-workers.These compounds are isomeric to the potent inhibitor nevirapine and available via the Smiles rearrangement of substrates that are intermediates used for the synthesis of nevarpine analogs. The deprotonated amide functionality in the rearrangement products displaces the chlorine at the 2-position to give the desired heterocycles in moderate to good yield. 

In the synthesis of the medicinally important benzodiazepine, an example of the use of an azide as an unisolated intermediate is given in Part I (p. 260). The azide may be isolated and then converted by a reductive cyclization into the diazepinone. 

Quinoxalinyl ketones have been prepared by application of the classical quinoxaline synthesis, an o-phenylenediamine being condensed with an appropriate 1,2,3-tricarbonyl compound. Reactions of this type do not provide an unambiguous synthesis of quinoxalinyl ketones, since an alternative mode of condensation is possible leading to a benzo-1,5-diazepinone. The latter possibility is eliminated in the example cited in Scheme 1 because NMR examination of the condensation product... 

Chiral 1,2-diazepines, for use as conformationally restrained peptide mimics, have been synthesized by preformation of aminopyrrole (103), from glutamic acid, then cyclization using conventional dec coupling to diazepinone (104) (Scheme 11) <92JOC3535>. Subsequent alkylation on the amide nitrogen has provided an acetic acid derivative (105), that was also prepared by the type bg synthesis (see Section 9.04.9.5.2). 

A similar approach has been used in the synthesis of diazepinone (169) from a phenyl-sulfonylpyradazinone precursor <91JHC369>. 

A synthesis of unusual 2-thio-4-oxo-2,3-dihydro-lH-l,3-diazepinones 52 utilized thiourea 51 and nitroallyhc acetate 50 along with methanol as a... 

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