Starting from simple 2-ethynylanilines 199 and o-bromobenzylamines 200,
complex indole-fused 1,4-diazepines 201 were easily and directly synthesized in
a single reaction vessel (Scheme 70) [115]. This transformation included a sequential Cu-catalyzed three-component condensation/indole formation/N-arylation process. o-Bromoheteroarylamines were also available for this domino process and
various indole-fused tetracyclic compounds were obtained.
Jørgensen reported an efficient three-component approach for synthesizing
phenothiazines (Scheme 71) [116], in which a C–S bond and two C–N bonds were
formed in one-pot under the catalysis of Pd 2 dba 3 /dppf. The transformation required
either microwave or conventional heating.
Ma et al. developed a sequentially controlled CuI/L-proline-catalyzed cascade C–S
and C–N bond formation process for assembly substituted phenothiazines 207
(Scheme 72) [117]. In this case using substituted 2-iodoanilines 205 and 2-bromobenzenethiols 206 as the coupling partners are essential for controlling regioselectivity.
Scheme 68 Synthesis of trans-3,4-dihydro-2H-1,4-benzoxazines via copper-catalyzed intramolecular N-arylation
Scheme 69 CuI-catalyzed synthesis N-substituted dihydro-2H-1,4-benzoxazine-3-(4H)-ones
from 2-halophenols and 2-chloroacetamides
Scheme 70 CuI-catalyzed synthesis of indole-fused 1,4-diazepines from 2-ethynylanilines and
o-bromobenzylamines
Scheme 71 Synthesis of phenothiazines via a Pd-catalyzed three-component reaction
114
Y. Jiang and D. Ma
complex indole-fused 1,4-diazepines 201 were easily and directly synthesized in
a single reaction vessel (Scheme 70) [115]. This transformation included a sequential Cu-catalyzed three-component condensation/indole formation/N-arylation process. o-Bromoheteroarylamines were also available for this domino process and
various indole-fused tetracyclic compounds were obtained.
Jørgensen reported an efficient three-component approach for synthesizing
phenothiazines (Scheme 71) [116], in which a C–S bond and two C–N bonds were
formed in one-pot under the catalysis of Pd 2 dba 3 /dppf. The transformation required
either microwave or conventional heating.
Ma et al. developed a sequentially controlled CuI/L-proline-catalyzed cascade C–S
and C–N bond formation process for assembly substituted phenothiazines 207
(Scheme 72) [117]. In this case using substituted 2-iodoanilines 205 and 2-bromobenzenethiols 206 as the coupling partners are essential for controlling regioselectivity.
Scheme 68 Synthesis of trans-3,4-dihydro-2H-1,4-benzoxazines via copper-catalyzed intramolecular N-arylation
Scheme 69 CuI-catalyzed synthesis N-substituted dihydro-2H-1,4-benzoxazine-3-(4H)-ones
from 2-halophenols and 2-chloroacetamides
Scheme 70 CuI-catalyzed synthesis of indole-fused 1,4-diazepines from 2-ethynylanilines and
o-bromobenzylamines
Scheme 71 Synthesis of phenothiazines via a Pd-catalyzed three-component reaction
114
Y. Jiang and D. Ma