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Axial chiral aryl indole carbazole derivative as well as preparation method and application thereof

A technology for aryl indole carbazole and its derivatives, which is applied in the field of axial chiral aryl indole carbazole derivatives and their preparation, can solve the problems of negligence in axial selective synthesis, and achieve excellent cyclic selectivity, The effect of high yield and high conversion rate

Active Publication Date: 2021-07-09
王磊
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, axially selective synthesis involving carbene insertion processes remains neglected

Method used

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  • Axial chiral aryl indole carbazole derivative as well as preparation method and application thereof
  • Axial chiral aryl indole carbazole derivative as well as preparation method and application thereof
  • Axial chiral aryl indole carbazole derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Synthesis of 3aa

[0038] Will dissolve in CHCl 3 2 mol% Rh in (1 mL) 2 (S-PTAD) 4 As a catalyst, diazonaphthoquinone derivatives (0.1 mmol, 1.0 equivalent) and pindolone [2,3-a] carbazole (0.15 mmol, 1.5 equivalent) undergo cross-coupling reaction at room temperature for 6 h, and the reaction After the end, the solvent was distilled off by rotary evaporation to obtain a light yellow solid 3aa with a yield of 68% and an enantiomeric selectivity of 99%.

[0039]

[0040] 1 H NMR (600MHz, CDCl 3 ):δ=8.24(d, J=7.8Hz, 1H), 8.16(d, J=7.7Hz, 1H), 8.07–8.03(m, 2H), 7.75–7.70(m, 4H), 7.75–7.70( m,1H),7.52(s,broad,1H),7.43–7.42(m,2H),7.40–7.33(m,3H),7.27–7.24(m,2H). 13 C NMR (151MHz, CDCl 3 ):δ=141.24,139.09,138.91,130.59,128.95,128.29,126.79,125.66,125.54,125.43,125.06,124.29,122.76,121.98,120.76,120.54,120.42,120.21,113.17,112.82,111.27,110.11.HRMS( ESI): calcd for C 28 h 19 ON 2 [M+H] + :399.1492, found 399.1487.

[0041] Note: 1 H-NMR and 13 C-NM...

Embodiment 2

[0042] Embodiment 2: the synthesis of 3ba

[0043] Will dissolve in CHCl 3 2 mol% Rh in (1 mL) 2 (S-PTAD) 4 As a catalyst, diazonaphthoquinone derivatives (0.1 mmol, 1.0 equivalent) and pindolone [2,3-a] carbazole (0.15 mmol, 1.5 equivalent) undergo cross-coupling reaction at room temperature for 6 h, and the reaction After the completion, the solvent was evaporated to obtain a light yellow solid 3ba with a yield of 62% and an enantioselectivity of 98%.

[0044]

[0045] 1 H NMR (600MHz, CDCl 3 ):δ=8.31–8.28(m,1H),8.11(dd,J=7.9,2.3Hz,2H),8.03(d,J=8.3Hz,1H),7.89(d,J=8.2Hz,1H) ,7.48(s,1H),7.42–7.40(m,1H),7.37–7.34(m,2H),7.28–7.26(m,1H),7.23–7.16(m,4H),7.12(d,J= 8.1Hz, 1H), 7.04–7.03(m, 4H), 6.14(s, 1H), 4.35–4.27(m, 2H), 2.03–1.98(m, 2H), 1.14(t, J=7.4Hz, 3H ). 13 C NMR (151MHz, CDCl 3 ):δ=147.14,144.81,141.33,139.26,128.90,128.10,127.86,127.52,126.37,125.97,125.78,125.59,125.22,125.12,124.39,122.68,122.54,122.02,120.68,120.60,120.38,120.00,117.33, 113.05, 112.99, 1...

Embodiment 3

[0048] Example 3: Synthesis of 3ea

[0049] Will dissolve in CHCl 3 2 mol% Rh in (1 mL) 2 (S-PTAD) 4 As a catalyst, diazonaphthoquinone derivatives (0.1 mmol, 1.0 equiv.) and pindolone [2,3-a] carbazole (0.15 mmol, 1.5 equiv.) undergo a cross-coupling reaction at room temperature for 12 h, and the reaction After the end, the solvent was evaporated to obtain a light yellow solid 3ea with a yield of 60% and an enantioselectivity of 98%.

[0050]

[0051] 1 H NMR (600MHz, CDCl 3 ):δ=9.22(d,J=9.6Hz,1H),8.27(d,J=7.5Hz,1H),8.10–8.02(m,1H),7.67(d,J=9.6Hz,1H),7.40 –7.35(m,1H),7.30–7.28(m,1H),7.22–7.16(m,1H),7.01(d,J=8.5Hz,1H),6.97(dd,J=7.0,1.1Hz,1H ), 5.98(s, broad, 1H), 4.52(q, J=7.1Hz, 2H), 1.49(t, J=7.2Hz, 3H). 13 C NMR (151MHz, CDCl 3 ):δ=168.04,152.76,141.17,139.35,133.53,130.18,128.96,128.76,127.65,127.60,127.38,126.93,126.24,125.74,125.51,124.06,123.03,122.28,121.60,120.82,120.36,120.31,119.97, 116.94, 113.97, 112.92, 111.58, 110.51, 61.97, 14.87. HRMS (ESI): calcd ...

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Abstract

The invention provides an axial chiral aryl indolocarbazole derivative and a preparation method thereof, the axial chiral aryl indolocarbazole derivative has a structure as shown in formula I. The axial chiral aryl indolocarbazole derivative disclosed by the invention is high in yield, has excellent enantiomer selectivity, and can be used for preparing the axial chiral aryl indolocarbazole derivative. The axial chiral aryl indolocarbazole derivative is selectively synthesized through an insertion reaction axis of N-H between catalytic molecules of Rh (II), and a research basis is provided for later functional derivation based on indolocarbazole alkaloids, development of novel materials and novel drugs and development of novel phosphoric acid catalysts based on the framework.

Description

technical field [0001] The invention belongs to the technical field of biomedicine synthesis, and relates to an axial chiral aryl indolecarbazole derivative and a preparation method and application thereof. Background technique [0002] Atropisomerism is a prominent chiral structural element arising from restricted rotation of single bonds and is ubiquitous in many natural products, drugs, chiral ligands, and catalysts. Therefore, the attractive properties and synthetic pathways of atropisomers have attracted great attention from chemical, pharmaceutical, and materials scientists around the world. In the past few decades, great progress has been made in the construction of various axial chiral scaffolds, especially in the synthesis of biaryls and styrenes containing C–C axes. In addition to the classical cross-coupling of two aryl structures, a number of novel and elegant strategies have been demonstrated to access these atropisomers, including de novo aryl synthesis, point...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D487/14C07D491/048H01L51/54
CPCC07D487/04C07D487/14C07D491/048H10K85/622H10K85/615H10K85/626H10K85/657H10K85/6572
Inventor 王磊何春年戴子茹任巧曹婷婷
Owner 王磊