The most recent quantity within the prestigious sequence The Chemistry of Heterocyclic Compounds, this paintings covers synthesis, reactions, homes, constitution, actual chemistry and application of monocyclic azepines.Content:
Chapter 1 creation (pages 1–8):
Chapter 2 Azepanes (Hexahydroazepines) (pages 9–116):
Chapter three Azepanones (pages 117–250):
Chapter four Azepanediones (pages 251–287):
Chapter five Tetrahydroazepines (pages 288–358):
Chapter 6 Tetrahydroazepinones (pages 359–402):
Chapter 7 Tetrahydroazepinediones (pages 403–411):
Chapter eight Dihydroazepines (pages 412–448):
Chapter nine Dihydroazepinones (pages 449–480):
Chapter 10 Dihydroazepinediones (pages 481–486):
Chapter eleven Azepines (pages 487–591):
Chapter 12 Azepinones (pages 592–606):
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Extra resources for Chemistry of Heterocyclic Compounds: Monocyclic Azepines: The Synthesis and Chemical Properties of the Monocyclic Azepines, Volume 56
Twenty years later6’ a similar type of reaction was applied (CH20/CF3C02H)to the silylamine 71 to give a very good yield of the azepane 72. An alkynylsilane (73)was also shownM to participate via an iminium ion, leading to the interesting allenic structure 74. 4 NHCH2Ph Si(CH3h (CH&SiCH2C=C(CH2)4NHiPr (73) bH2Ph L,,,) I (74) Palladium chemistry has helped in promoting radical-like cyclisations of ahalo esters and ketones. The ~ ~ radical-like features of this type of reaction were revealed by Curran and Chang,68 who demonstrated that identical product mixtures were obtained from unsaturated a-iodocarbonyls using either Pdo or (Bu3Sn)2;compound 78 along with several others was isolated from the iodo Azepanes (Hexahydroazepines) 19 (77) (78) (79) ester 79.
Substitution at 2-Position This area has been extensively investigated. Seebach er showed that Nnitrosoazepane (9, R = NO) could be deprotonated at C-2 (LDA/THF/ -80 "C) and reacted with electrophiles; for example benzophenone gave 130 [R' = NO, R2 = CH(OH)Ph2J. '23 It had previously been shown'" that tributyltin chloride participated in these reactions leading to the isolation of 130 (R' = C02'Bu, R2 = Bu3Sn). 1267127 The products are C2-alkoxy-Nformyl- or -N-acetylazepanes (130, R' = CHO, COCH3, R2 = OCH3 or OC2H5) depending on which alcohol was employed.
G. OPh, OCSSPh) allowed thermal reactions to proceed which relied on the ease of carbonyl sulphide (COS) elimination. @ For example, the carbonate 111 reacted with the appropriate organoaluminium (111) (112) (113) reagent (R = CH3 or "BuC=C) giving azepanes (112, R = CH3 or "BuCrC) in good yields. As discussed in Section 3, derivatives of cyclohexanone oximes undergo Beckmann rearrangement/reduction in 'one-pot' processes which overall could be regarded as ring expansions. 85Indeed, oximes themselves have been subjected to the trialkylaluminium/diisobutylaluminiumhydride protocol previously (Section 3) described for oxime sulphonates.
Chemistry of Heterocyclic Compounds: Monocyclic Azepines: The Synthesis and Chemical Properties of the Monocyclic Azepines, Volume 56