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Новые достижения в химии и химической технологии растительного сырья. Материалы III всероссийской конференции. Книга 2 [2007]

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@$3>? A%"/ #&0%( +&,"%8 .-(3"0> (1;#$'($ "0",$''"0%$/ +$&2<(( )(*+","+(+"-&'(.-"2(03$'(. (+$)("- ( 0%$+$"0$3$2%(-'"0%(, &0(44$%- +(#$02"/ ('*;2<(( 0 ;#&0%($4 "9%(#$02( &2%(-'")" <$'%+&) *"0%;9'86 [2] (1 2&0%"+"-")" 4&03& 0;,0%+&%"- 1 ( 2, ",;03"-3$''86 9+(0;%0%-(- $4 )"4"&33(3>'"/ ( ;*&3$''"/ "% *-"/'"/ 0-.1( )(*+"20(3>'86 )+;99.

B 2$0%-$ )(*+","+(+;?7$)" +$&)$'%& (09"3>1"-&3( *(,"+&' - +&0%-"+$ THF [3]. C(*+","+(+"-&'($ *-"/'"/ 0-.1( 0"$*('$'(/ 1 ( 2 0 9"03$*;?7(4 "2(03$'($4 ",+&1"-&-5(60. ,"+"+)&'(#$02(6 ('%$+4$- *(&%"- 7$3"#'84 +&0%-"+"4 H2O2 9+(-$3" 2 0""%-$%0%-;?7(4 +$)("- ( *(&0%$+$"4$+'84 1,3-(3), (4) ( 1,4-(5), (6) *("3&4.

OH

1. NaBH4, BF3•OEt2

Me(CH2)5 (CH2)7R 2. H2O2, NaOH

91-99%

1 R = Me

2 R = CH2OH

OH OH

 

OH

Me(CH2)5

(CH2)7R

+ Me(CH2)5

R,S (CH2)7R

R,S

 

 

S>R

 

S>R OH

3

R = Me

5

R = Me

4

R = CH2OH

6

R = CH2OH

20

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5

TsOH/C6H6,

 

2

5

quant.

Me(CH2)5

O

(CH2)7Me

 

 

 

7

 

9 /*5$%"#(8@ 4.$01%'@ 1$1%'*)#%"G/%'("- 7 4)*('58 '1","- /*5$- %"#' !-2 ) !-5, ' 1'0&$ #-/@ J-'1","- /*5$%"#' CH2-*%/.. .%) !-2 ) !-5 $%&'#-41$%$")+",$%' 4,$I$(8, ." 4%'-($()H 4 !"#-)+",$%",, (' 2– 2,5 ,.#. - 45'2"."5?(/H "25'41?. ="#"2(8$ 45'2"."5?(8$ 4,$I$()3 4)*('5"- /0'+'((8@ '1","- /*5$%"#' $%&'#-)+",$%"- ) .%"1"("- .%) >1)@ '1",'@ /*5$%"#' )+-$41(8 [5–8] #53 %3#' 2,5-#)+',$I$((8@ .%")+- -"#(8@ 1$1%'*)#%"G/%'(', ' 1'0&$ [9] 4/5?G"5'(' ) 4)5'6)05".$(1'('. 9 >1)@ %'2"1'@ .%)$, 6)05)+'6)) )4."5?+/$143 .%) /41'("-5$()) 0"(- G)*/%'6)) '4),,$1%)B$40)@ '1","- #)'41$%$",$%(8@ 1,3- ) 1,4-#)"5"- [10–13], .%)B$, "2%'+"-'()$ 6)05"- 4".%"-"'$143 )(-$%4)$7 1"5?0" "#("*" )+ #-/@ )5) "2")@ [5, 14] '4),,$1%)B$40)@ 6$(1%"- #)"5"-.

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21

!"#$#% !"#$%-&'#$() *)(+,"!%-.(" (2R,5R)- &-& (2S,5S)- /0!0"$()012 *!)1 "(")!3&+)#41)!0! 7 [14]. 5' /"#3# ,-(+1(", 6"# *)& &,7#+0#8 (R)-9#04&31)!:&& !"#$! ;-7 +-! 1, !"#$ ;-10 *)(#<-!- +!2=(3# +-! , 16("#$ &0%(),&& <1+(" &$("> (S)-9#04&31)!:&2 '!- $(,"&"(-(8. &'% (()*+)-&'#$() "(")!3&+)#41)!0! 7 *)& &0%(),&& -2- <#3# &' !,&$$(")&6(,9&7 !"#$#% *)(+,"!%-.(" /0!0"$() , (R)- & (S)- 9#04&31)!:&(8 !"#$#% ;-2 & ;-5, 6"# ,##"%(","%1(" , 16("#$ &0%(),&& (R,R)-/0!0"$()1, *)(+,"!%-.2=(3# dl-*!)1 +-!. ;#+()?!0&( ()*+- +-! ,#,"!%-.(" 70%, dl-+-! – 30%.

@(0!,A=(00A8 +- 2 % )(!9:&& 3&+)#<#)&)#%!0&.-#9&,-(0&., !0!-#3&60# 1, #<)!'1(" ,$(,> #9"!+(9!0-(1,10RS,12R)-")-! 4 (53%) & #9"!+(9!0-(1,9RS,12R)-")-! 6 (47%).

;(-(9"&%0!. <(0'&-&+(0#%!. '!=&"! [12, 13] 1,3-+-! 4 *)&%#+&" 9 ,'%,,'%/!"#$%,!"#$%-,"()(#&'#$()0A$ *#+19"!$ +&!-9&-4(0&-'!- $(=(00#3# 1,3-+ ,!0! 8.

 

 

 

 

Ph

 

 

 

 

 

PhCHO, ZnCl2,

O 2

O

 

 

4

+

6

6

4 R,S

(CH2)8OH

+ 6

Na2SO4

Me(CH2)5

 

 

 

 

 

 

 

 

 

 

 

8

S>R

 

 

B(0'&-&+(0&)#%!0&( ,$(,& *)#+19"#% ,'%-3&+)!"!:&& ,#(+&0(0&. 2 *#'%#-&-# 7)#$!"#3)!4&6(,9& )!'+(-&"> & &+(0"&4&:&)#%!"> 1,3- & 1,4-+-A. 5'%(,"0#, 6"# :&9-&'!:&. % 1,3-+ ,!0 8 *)& <(0'&-&+(0#- %#8 '!=&"( *)#7#+&" <(' &0%(),&& #*"&6(,9& !9"&%0#3# !"#$! [12, 13, 15] & % 0(8")!->0#8 ,)(+( !-9&-'!$(=(00A( 1,3-+ ,!0A &$(2" 1,- "#86&%12 9#04#)$!:&2 «9)(,-#», % 9#"#)#8 %01")(00(( %)!=(0&( 3(- "()#:&9-! '!"#)$#?(0# [16]. C(-&6&0! 7.,. *)#"#0! *)& Ph-3)1**( #<#- &7 ,"()(#&'#$()#% (5,56 $.+.) 19!'A%!(" 0! 9#04#)$!: 1,"#8- 6&%#,"> & /9%!"#)&!->012 #)&(0"!:&2 4(0&->0#8 3)1**A % #<#&7 ,"(- )(#&'#$()!7 [17, 18]. C 13-()#+0#$ ,*(9")( + ,!0! 1 &$(2",. +%! 0!<#)! ,&30!-#%, #"0#,.=&(,. 9 +&!,"()(#$()0#8 *!)( ,# '0!6&"(->- 0A$ *)(#<-!+!0&($ ,"()(#&'#$()! , <#-(( ,-!<#*#->0A$& 7.,. !"#$#% 13-()#+! :&9-! ;-2 (+, 100,57 $.+.), ;-4, ;-6 (+, 77,10 $.+.), 9#"#)A(

22

!"#$%'( )# *+,"(-.+#/0)!' -.+1)(#2+' *&!3 #/"+/0)%3 $#415(+- (1/16, 5--(&1(5(&!'7+3 !"#,!"#-+$-41.! 5 $$$ -.+1)(#2+16 $#415(+(1- /16. 8.+ (R)-"-)9+:!.#2++ -;(+<15"+ #"(+&)-:- 21)(.# =-12 (.+-/# 4 & !"# ($$)-=-4, =-6 5(1.1-+$-41.1 #5+441(.+<15"+6 #(-4 =-4 +411( (S)- "-)9+:!.#2+'. >-/11 5+/0)-;-/0)%1 3.5. #(-4-& !:/1.-*# 2+"/# =-2 (*, 99,1 4.*.), =-4 (*, 71,34 4.*.), =-6 (*, 77,92 4.*.) -()-5?(5? " %&'(#

($')-=-4, =-6 5(1.1-+$-41.!, & "-(-.-4 #"5+#/0)%6 #/"+/0)%6 $#415- (+(1/0 ;-*&1.@1) 5(1.+<15"-4! &$#+4-*165(&+' 5 #(-4-4 =-2 2+"/#. A ,(-4 5/!<#1 #"5+#/0)#? -.+1)(#2+? $#415(+(1/? ;.+ #(-41 =-4 5--(- &1(5(&!1( (R)-"-)9+:!.#2++. =-*1.@#)+1 !"#,!"# ($$$)- + %&'(#,%&'(# ($'$)-5(1.1-+$-41.-& 5-5(#&/?1( 75 + 25% 5--(&1(5(&1))- + 5&+*1(1/0- 5(&!1( - ;.1+4!715(&1))-4 -B.#$-)++ (10S,12R)-(.+-/# 4, !"#$%? )# ,)#)(+-5;12+9+<)-5(0 -B.#$-)+? 1,3-*+-/#.

1,3-C+-/ 3 ;.1*5(#&/?1( 54150 *+#5(1.1-41.-& & 5--()-D1)++ 66 : 34, (.+-/ 6 – 61:39. =.#&)+(1/0)%6 #)#/+$ 5;1"(-& EFG 1,3- + 1,4- *+-/-& 3 + 5 5- 5;1"(.#4+ *+-/-& 4 + 6, 5-*1.@#7+3 "-)21&%1 :+*.-- "5+/0)%1 :.!;;%, ;-"#$%(, <(- &- 5/!<#?3 ;.1-B/#*#/+ *+#5(1.1-- 41.% 5 (S)-"-)9+:!.#2+16 -B.#$!'7+35? #5+441(.+<15"+3 21)(.-&.

H#"+4 -B.#$-4, ;-/!<1))%1 *#))%1 5&+*1(1/05(&!'( - (-4, <(- &

.1#"2++ :+*.-B-.+.-)+?--"+5/1)+? ;.-+$&-*)%3 .+2+)-/1&-6 "+- 5/-(% :+*.-"5+/0)#? :.!;;# ;.+ -;(+<15"+ #"(+&)-4 #(-41 !:/1.-*# )1$)#<+(1/0)- &/+?1( )# .1:+-51/1"(+&)-5(0, )- +:.#1( .-/0 +)*!"(-.# #5+441(.++ ;- "#@*-4! +$ #(-4-& !:/1.-*# *&-6)-6 5&?$+. I-)21? :+*.-"5+/0)#? :.!;;# & 4-/1"!/1 5;+.(# 2 ;.#"(+<15"+ )1 -"#$%( &/+?)+? )# ;.-(1"#)+1 *#))-6 .1#"2++.

!"#$%'%&

1.F+3#6/-& >.F., >!B)-& J.K. >-.-.:#)+<15"+1 5-1*+)1)+? & -.:#)+- <15"-4 5+)(1$1. F., 1977. 516 5.

2.LD4!.#(-& M.J., N#.+5-& G.E., O#?341(- P.N., >-24#) Q.8. + *.. L55/1*-)+1 -$-)-/+$# ;.-+$&-*)%3 .+2+)-/1&-6 "+5/-(% + (.#)5- 9-.4#2+? ;.-*!"(-& -$-)-/+$# & !5/-&+?3 .1#"2++ >#.(-)# // N+4+? ;.+.-*)%3 5-1*+)1)+6. 2005. R6. =. 529–534.

3.Schlesinger H.I., Brown H.C., Hoekstra H.R., Rapp L.R. Reactions of diborane with alkali metal hydrides and their addition compounds. New syntheses of borohydrides. Sodium and potassium borohydrides // J. Amer. Chem. Soc. 1953. V. 75. R1. P. 199–204.

23

4.Reppe W. Äthinylierung // Liebigs Ann. Chem. 1955. Bd. 596. S. 1–224.

5.Mihailovic M.Lj., Mamuzic R.I., Zigic-Mamuzic Lj., Bosnjak J., Cekovic

Z.Assignment of cis-trans configuration to constitutionally symmetrical 2,5-dialkyl-tetrahydrofurans // Tetrahedron. 1967. V. 23. !1. P. 215–226.

6.Pilli R.A., Riatto V.B. Diasteroselective synthesis of 2,5-disubstituted tetrahydrofuran derivatives // Tetrahedron: Asymmetry. 2000. V. 11. !18.

P.3675–3686.

7.Yoda H., Mizutani M., Takabe K. An efficient and stereoselective conversion of lactones to substituted cyclic ethers // Heterocycles. 1998. V. 48. !4. P. 679–686.

8.Shi H., Liu H., Bloch R., Mandville G. A novel efficient and stereoselective synthesis of cis- or trans-2,5-disubstituted tetrahydrofurans // Tetrahedron. 2001. V. 57. !45. P. 9335–9341.

9."#$%$&$' (.). "*+%+,&$-$. $ /#+0*%,/0,#$. 123 14 $ 13" #%,$5- 6,7'8& /9:;<,:='= $ /$:=>$0:,#+'*='=. ?$/. … 0='7. &$-. '=90. –

@<=, 1985. 104 /.

10.A,*=#,6 ).2. "*+%+,&$-$.. 2., 1998. 464 /.

11.Dounay A.B., Florence G.J., Saito A., Forsyth C.J. Direct synthesis of substituted tetrahydrofutans via regioselective dehydrative polyol cyclization cascades // Tetrahedron. 2002. V. 58. !10. P. 1865–1874.

12.Sharma M., Brown R.K. The preparation of 4,6-O-benzylidene-D-glucal and the reaction of methyllithium with methyl 2,3-anhydro-4,6-O- benzylidene-B-D-allopyranoside // Canad. J. Chem. 1966. V. 44. !23.

P.2825–2835.

13.Kuzuhara H., Ohrui H., Emoto S. Synthesis with azido-sugars. 2. Conversion of D-glucose to (+)-desthiobiotin // Agr. and Biol. Chem. 1971. V. 35. !1. P. 8–17.

14.Mihailovic M.Lj., Gojkovic S., Cekovic Z. Stereochemistry of cyclic ether formation. Part I. Stereoselective intramolecular cyclisation of aliphatic disecondary 1,4-diols and their sulphonate esters tetrahydrofurans // J. Chem. Soc. Perkin Trans. Part I. 1972. !22. P. 2460–2464.

15.C,D+*0,6 4.C., "6$%$7,6 E.F., G%-,:+'0, 2."., H$I,6 J.". @K:+6,- 78 6 /$'*+5+ #%$%,7'8& /,+7$'+'$L. 2., 1984. 288 /.

16.Eliel E.L. Conformational analisis in heterocyclic systems. Recent results and applications // Angew. Chem. 1972. Bd. 84. !17. P. 739–750.

17.C:,D0,6 ).)., (=*8#,6 M.C., 3=&-=*9::$' E.N., )=<$'= 3.2. $ 7%. ):$.'$+ <=5,6,K, /,/*,.'$. (K=5, %=/*6,%, *6+%7=. <=5=) '= 0,'<,%- -=>$$ 2-O*$'$:-1,3-7$,0/=',6. ?=''8+ 123 // P9%'=: ,QR+L &$-$$. 1998. S. 68. )8#. 1. ". 140–146.

18.C=-$*,6 T.T. E*:=/ /#+0*%,6 123 #%,/*%='/*6+''8& $5,-+%,6. C=-

5=';, 1978. S. 1. 205 /.

24

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E-mail: kataev@iopc.knc.ru

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25

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O

O (CH2)n

O

O

(CH2)n O

 

O

O

O

O

CO2H

CO2H

 

CO2H

O

 

O O

 

 

 

 

1

2

 

n = 4 (3), 6 (4), 8 (5)

4$9%+*9:#&-: ;%$8%"#': 8-+#$?'+9- 5

4$9%+*9:#&-: ;%$8%"#': 8-+#$-

 

?'+9- 3

@$9%% *)$A&78 1($1$A$8 ($9*B%&': 8-+#$?'+9$,, , +$"$#7> '.$- 1"%,'$9=&7% C#-;8%&"7 1$%)'&%&7 19$D&$EC'#&78' 1(%21%#-8', :,- 9:%"1: ,.-'8$)%21",'% 1 >9$#-&;')#')-8' ),*>$1&$,&7> +-#A$&$,7> +'19$" (#$)*+"- ($9&$;$ ,$11"-&$,9%&': '.$1"%,'$9- -9F8$;')#')$8 9'"': 6. 5%-+?'F (#$,$)'9' , +'(:G%8 CCl4, (#$)*+"7 7–9 ,7)%9'9' +$9$&$B&$2 >#$8-"$;#-C'%2 &- 1'9'+-;%9% 1 ,7>$)-8' 16, 33 ' 26% 1$$",%"1",%&&$. H /0-1(%+"#-> (#$)*+"$, '8%F"1: ($9$17 ,-9%&"&7> +$9%A-&'2 19$D&$EC'#&$2 ;#*((7 ' $"1*"1",*F" ($9$17 ,-9%&"&7> +$9%A-&'2 ;#*((7 I6. 4$9%+*9:#&-: 8-11- (#$)*+"$, ($)",%#D)%&-

26

!"##-#$%&'()!%'(*+%#&* (,- ./0 7 * 9, MALDI ./0 8). 1)/%&2/0(3"0 4%)!%'(*0 !"&()5*&/" 9 2#'"3)6/%3" !%').)! 789.

O

OH

 

O

(CH2)n

O

 

O

 

CH2 CH2

 

 

 

O

 

O

 

 

 

O

 

 

 

CH2

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

CH2

 

 

 

 

 

 

 

 

 

CH2

 

 

H2C

 

 

 

 

 

 

CH2

CO H

CH2OH

O

(CH2)n

O

CH

H2C O

 

CH2

2

 

 

 

2

CH2

 

 

 

O

 

O

 

 

O

 

1

6

 

n = 1 (7), 4 (8)

 

 

9

 

:(%;.% +%! $%(%<'* & #*3'%=2 !"&()5*&/*+%#&*> $()*=6).3?> *=)#'%6*)/" # 4*.("=*.3?! * 4*.("=)33?! @("4!%3'"!*, !? *=2+*/* (%"&5*)332A #$)#)B3)#'C *=)#'%6*)/" 1 * 3%&)')(?> %4) $()*=6).3?> 6 )'3)D%3** 4*.("=*3 4*.("'" * # 2.*6/%3*%! )B3"(2;*/*, +') D*()- &) *=6%#'3"0 6 /*'%("'2(% (%"&5*0 E@*()6 &"(B)3)6?> &*#/)' # 4*.("- =*3 4*.("')!, $(*6).0F"0 & *> 4*.("=*."! [6], $()'%&"%' 6 #/2+"% E@*- ()6 *=)#'%6*)/" # )B("=)6"3*%! "=*3)6 10. 8"! *=)#'%6*)/ 1 (%"4*(2%'

# 4*.("=*3 4*.("')! '"&;% # )B("=)6"3*%! "=*3" 10 (R= OH). :(* 6="*!).%<#'6** *=)#'%6*)/" 1 # .*4*.("=*.)! ".*$*3)6)< &*#/)'? # 6?>).)! 23% B?/) 6?.%/%3) B*#-$()*=6).3)% 12. G'!%'*!, +') $()-

.2&' 6="*!).%<#'6*0 *=)#'%6*)/" 1 # .*4*.("=*.)! !"/)3)6)< &*#/)- '?, " *!%33) B*#-$()*=6).3)% 11, !? (%4*#'(*()6"/* ')/C&) 6 (%"&5*- )33)< #!%#*. H?.%/*'C %4) 3% 2."/)#C ! ("=("B)'&" (%"&5*)33)< #!%#* $(*6).*' & "=*32 10 (R= OH).

N N

 

O

O

 

 

 

1. SOCl2

N2H4

 

2. ROH

C O

CH3OH

C O

OH

OR

 

 

 

O

C

C

OR

O OR

 

 

 

10

27

O O

N-NH-C-(CH2)n-C-NH-N

C O

O C

n = 1 (11), 4 (12)

OH

OH

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

.&:$71( 2&7# /#% /( $",(*+(/.

O O

1 : 1

 

O

C

NH HN C

( 14 )

 

 

 

 

N2H4

 

 

 

 

O

 

O

 

 

 

 

 

C O

!"#$%&'

N

N

 

 

 

N

NH

O

 

 

 

 

Cl

 

 

 

 

 

 

C

( 13 )

1 : 20

 

 

 

"("

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

O C

NH

NH

C

O

C

NH

N

 

 

 

 

 

O

 

 

( 15 )

B(#7:$() 01&.#/-$'$.$'# 13 * <+$1(/-1$7&1(% , CCl4 961 2&13- 4(/ '$<A$. 16, ,"#$%&'()*+,$(% 7&+&.&-& * '$-$'.#"$'&% %#1&/&,&) 7$*1&+6 , 7$2;C(% <+#/&1( * ,60&'&% 35% 961 2&134(/ %#7.&:$71 17.

!"#$%&'()*+,$( 01&.#/-$'.$'# 13 * '$-#'.$"$'&% #'$2$/&,&) 7$*1&+6 "#,$*$+ &+ *&&+/&5(/$; .(#-(/+&,. B(#7:$; $0 <7,$%&1;./60 7&1$4(*+, , 2$.$'$/( 2.$ 7&%/#+/&) +(%2(.#+3.( 2.$,&'$+ * ,60&'&% 25% 7 '$-$'.#"$'3 18. B(#7:$; 01&.#/-$'.$'# 13 * ',307.#+/6% $"-

28

!"#$%& '()('*+,('+ -*(.%'(# /01, 2 ."3%'%& 32%, $ &+$*%4($5/ 19. 6 78-2-1$#*1 !(2--*%(,.%'9%)% 18 %#2/#2#./1# -%5%2+ .+519#9"3 $%51- !+9(: $+*!%$2(5;9%: )*/--" (,%2#1.(%5+ (1693 2&-1) ( 9+!5<'+1#2= -%5%2+ -%)5%>19(= 1)% $1#%)*/--" -*( 17372&-1. 6 78-2-1$#*1 &+$*%- 4($5+ 19 %!1 %9( %#2/#2#./<#, ,+#% 9+!5<'+<#2= -%5%2+ -%)5%>19(= -*( 1665 2&-1, 2%%#.1#2#./<>+= .+519#9"& $%51!+9(=& 2.=,( C=N ( -%5%2+ «+&(' II» -*( 1528 2&-1. ?#*%19(1 -*%'/$#%. -%'#.1*0'19% #+$01 '+99"&( &+22-2-1$#*%&1#*(( (@A) ( B51&19#9%)% +9+5(,+.

 

O

O

NNHC(O)CH2C(O)HN N

 

O

 

 

 

C O

C O (CH2)2 O C

C O (CH2)2 O C

Cl

O

O

O

O

 

13

 

16

 

17

 

 

O

O

 

 

 

 

 

( 18 )

 

O

C NHNHC(O)(CH2)4C(O)HNHN C

 

 

O

O

 

 

 

 

C O

 

NNHC(O)(CH2)4C(O)HN N

 

 

 

 

 

Cl

 

 

 

( 19 )

( 13 )

 

 

 

 

 

 

 

 

 

C NHNHC(O)(CH2)4C(O)HNHN C

 

 

 

O

O

 

!"#$%'%&

1.C5;D%92%. 6.C. ( '*. // !"#. 1998. E. 68. 6"-. 11. ?. 1813–1821.

2.Lee ?. et al. // Planta Med. 2001. Vol. 67. P. 796–799.

3.Chen S., et, al. // Int J. Cardiol. 2004. Vol. 97. F2. P. 1–75.

4.Kelmer Bracht A., et al. // Pharmacol. Biochem. 1985. V.. 34. F6. P. 873–882.

5.8+#+1. 6.G. ( '*. // #$%. &'(%. )*(+',. 2006. E. 40. 6"-. 9. ?. 12–13.

6.Paulsen H. et al. in «The chemistry of Hydrazo, Azo and Azoxy Groups», ed. S.Patai, Interscience. New York. 1975. V. 2. Ch. 10. P. 527–532.

29

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