Phosphorus-containing derivatives of indole and pyrole (review). (англ

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		R1		4	6 7
		ClPR2R3		R	PR R
		2			+
	N	R
			N	R5	N R
	X		Y		H
	1				4
			3

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					Z
1a	5
	NEt3	N
						N
		H				H
		6				7

Z = O, S

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	O			Z	O
	P	Ar		P	Ar
	O	[O]			O
	N		N
	P		P	Z
O	O		O	O
	Ar		Ar
	8
			9

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						O
OH						OP	Ar
						O
					3 (5)				O2
N	O		N		N	O		N
H	10		H			O		O	Ar
					P	Ar		P
						O	11	O
		O O					O O
		OP	Ar				OP Ar
		O			2EtOH		O
	N	O		N		N	O		N
		O		O	Ar	H			H
O	P	Ar		O P				13
		O		O
			12

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	CH2NMe2	CH2NMe2
	ClP(OEt)2
N		N
H	(EtO)2PO(Me)C= CHC(O)Me
14		P(OEt)2
		15
	CH2NMe2	CH2NMe2
	N	N
	(S)P(OEt)2	(O)P(OEt)OCH=CCl2
	16	17

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		1a, 1c	+ Cl PR'
			2
	R'
	P N			PR'
N	R	+	N	+ R'P	N
	R			R	R	2
H			H	2
	18		19			20

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HNEt2	+ NEt3	3d
	ROH + NEt3			S	N
			3a		(S)P(OR)2
				Cl3 CCHO
N			RI		22
PCl2
21
			N	N
			(O)PR(OR)	(O)P(OR)OCH=CCl2
			24
				23

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			OR	CH2X
		O	P		OH
N	CH2X	ROH	O	O	+
O P	OH				N
O					H
			O	O
	O
O	O

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	PBrn		P(O)R2
N	Me	N	Me
Me	3–n	Me	3–n

28a,b

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28 a R = NEt2, b R = Ph

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3					+PCl3								P
					_	3KCl						3
							29

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PBr2

N

PBr3

N

PBr2

N

Me

Me

Me

30a

PBr2

30b

O

Ph2P N

PPh2

R2(X)P

N

Ph2P N CH

Me

Me

Me

30c

30d

30e

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	CH
N	N P(X)Ph
Me	PPh2
31	32

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		Me				Me
		PCl3				2EtOH
N		AlCl3	Cl2P		N
Me					Me
			Me			Me
			S
(EtO)	P	N		(EtO)2P(S)		N
2		Me				Me
					34
		33

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R'

Cl2P

R' X P

R''

R''

PCl3

R''

2

R'

N R

N R

N R

Me

Me

Me

36a–c

37

X = OH

a R = R' = R'' = H;

38 X = NR2

b R = R'= H, R'' = Me;

39

X = OR

c R = R'= R'' = Me

X2(Z)P

R''

38, 39

Z ( O, S)

R'

N

R

Me

40 X = NR2, Z = S; 41 X = OR, Z = O

(RO)2P(O)

41

Cu2Cl2

R = R'= R'' = H C5H5N

N

41a

Me

R(RO)(O)P

R(RO)(O)P

39

RX

Cu2Cl2

R = R'= R'' = H

N

C5H5N

N

Me

Me

42

42a

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(EtO)2(O)P	(EtO)2(O)P
N	N
H	H
43	43a

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O2N		O2N
		MnO2
(EtO)2(O)P	N	(EtO)2(O)P	N
	H		H
	44		44a

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	SH	SPRR'	SH
	ClPRR'		+
	NEt3
N		N	N
H		H	PRR'
45		45a,b
			46a,b

a R = R' = OAlk, b R = R' = NAlk2

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			CH						CH(Cl)P(O)Ph2
						ClPPh2
N						N
R						R
47a,b						48a–c
a R = H; b R = Ac						a R = PPh2; b R = Ac; c R = H

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		O				Cl
			ClPPh2			P(O)Ph2
N O				N O
R				R
49a,b				50a,b
a R = H; b R = Ac				a R = PPh2; b R = Ac

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5		O	O
		[O]
49a
NEt3	N	O	N O
	R		R
	51a		51b
	R = PO2Ar	R = P(O)O2Ar
			O
	OP(O)2Ar		OP(O)2Ar
5		Cl O2	Cl
49a
	N	O	N O
	H		H
	52a	80oC	52b
		O	P(O)2Ar
			Cl
		N	O
		H
		52c

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			Cl2POR	N
N
		CH2CH2OH			CH CH O
CH2N				CH2N	2	2
		CH2CH2OH				POR
				53	CH2CH2O

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Br	N N	.HCl	Br		N N
	H	Cl2POEt			P
						O
N	O	O	3NEt3	N	O EtO
H	HO			H		O
					54

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	R'			R'
		(R2N)3P
		_ R NH		R''
N	R''	2	N

H

P(NR2)2

3d–i

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	H	PNEt2
		N
	N
		3P(NEt2)3
	N	N
	H	PNEt2 55

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P(O)(OH)2

	3d R'Hal	H2O(H+)
	N		N
			H
	+	_	56
	R' P(NR2)2Hal

57a–c

57a–c a R = R' = Et; b R = Et, R' = Pr; c R = R' = Bu

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Br	P(OEt)3_	(EtO)2(O)P
N	Me NiCl2	N	Me
H		H
Br		58
	P(OEt)3_	(EtO)2(O)P
N	NiCl2	N	Me
	Me
H		H
		59

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