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ÂÎË×ÂÕËÚÇÔÍËÏË Ë ÂÓÑÏÂÕËÚÇÔÍËÏË ÂÊËÆÂÏË.
R1C NR2 R1 N NHNH2 R1 N
R1CN + N3R2 N
HNO2
N N N
N N N N
R2 N R2 N

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ËÔÒÑÎßÊÑÄÂÐÞ ÐËÕÓËÎÞ ÓÂÊÎËÚÐÑÅÑ ÔÕÓÑÇÐËâ.103 ë 105 ±ÓÑÙÇÔÔ ªÐÕÇÓÇÔÐÞÌ ÔÒÑÔÑà ÒÑÎÖÚÇÐËâ ÂÐÐÇÎËÓÑÄÂÐÐÞØ ÕÇÕÓÂÊÑ-
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ÛÇÐÐÑÏ ÆÂÄÎÇÐËË (10 ÍÃÂÓ).30, 31, 106, 107 ÎËÐÂ Ô Ò-ÕÑÎÖÑÎÔÖÎß×ÑÐËÎÂÊËÆÑÏ Ä ÖÔÎÑÄËâØ ÏÇÉ×ÂÊÐÑÅÑ
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ÍËÏË ÂÊËÆÂÏË ÑÃÓÂÊÖÇÕÔâ Ä ÓÇÊÖÎßÕÂÕÇ ÄÊÂËÏÑÆÇÌÔÕÄËâ +
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ÐÑÔÕß ÐËÕÓËÎÑÄ Ë ÑÓÅÂÐËÚÇÔÍËØ ÂÊËÆÑÄ.
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ÓÂÊÑÎÑÄ ËÏÇÇÕ ÓÇÂÍÙËâ ÍÇÕÑÐÑÄ Ô ÂÊÑÕËÔÕÑÄÑÆÑÓÑÆÐÑÌ ÍËÔÎÑ-
R
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ËÊÖÚÇÐÞ ÑÚÇÐß ÒÑÆÓÑÃÐÑ. ±ÑÍÂÊÂÐÑ, ÚÕÑ Ä ÔËÐÕÇÊÇ 1,5-ÆËÊÂ- N N
ÏÇÜÇÐÐÞØ ÕÇÕÓÂÊÑÎÑÄ ÏÑÅÖÕ ÃÞÕß ËÔÒÑÎßÊÑÄÂÐÞ ÍÇÕÑÐÞ N N
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ÃÑÓÂ,111, 112 ÚÇÕÞÓÇØØÎÑÓËÔÕÞÌ ÕËÕÂÐ.113 ¥ÑÎÅÑÇ ÄÓÇÏâ ÑÔÐÑÄ- ÄÖá ÑÚÇÓÇÆß àÕÑ ÓÇÂÍÙËâ ËÊÑÙËÂÐÂÕÑÄ Ô ÂÊËÆÑÏ ÐÂÕÓËâ 123 ËÎË
µÔÒÇØË ØËÏËË 63 (10) 1994 851

ÕÓËÏÇÕËÎÔËÎËÎÂÊËÆÑÏ,124 ÕÇÓÏËÚÇÔÍÂâ ÒÇÓÇÅÓÖÒÒËÓÑÄÍ ³ØÇÏ 1

5-ÂÊËÆÑ-1,2,3-ÕÓËÂÊÑÎÑÄ 125, 126 Ë ÆËà×ËÓÑÄ 3,3-ÆËÂÊËÆÑÏÂÎÑ-
Br
ÐÑÄÑÌ ÍËÔÎÑÕÞ.127
N3 RC6H4NH N CH CH N NHC6H4R + N3 Br
D CH3OOCC NCH3
CH3OOC C COOCH3
N N Br
N3
N
N C C N
³áÆ ÉÇ ÔÎÇÆÖÇÕ ÑÕÐÇÔÕË ÒÓËÔÑÇÆËÐÇÐËÇ ËÑÆÂÊËÆÂ Í ÐÑÓÃÑÓ- RC6H4N NC6H4R
ÐÇÐÖ 128 Ë 1-ÏÇÕËÎÇÐ-4-(ÕÓÇÕ-ÃÖÕËÎ)ÙËÍÎÑÅÇÍÔÂÐÖ 129 Ä ÂÙÇÕÑ- N N N N
ÐËÕÓËÎÇ.
R = H, OCH3, Br, Cl
CH3CN
(CH3)3C CH2 + IN3
³ØÇÏ 2

N N N N
CH2I (CH3COO)4Pb N
(CH3)3C C6H5N N C6H5N
N
N C CH3 N N N N
N N NH2
N
NCC N
¯ÇÆÂÄÐÑ ÃÞÎÑ ÒÓÇÆÎÑÉÇÐÑ ÇÜÇ ÐÇÔÍÑÎßÍÑ ÏÇÕÑÆÑÄ ÒÑÎÖ- N NC6H5
ÚÇÐËâ 1,5-ÆËÊÂÏÇÜÇÐÐÞØ ÕÇÕÓÂÊÑÎÑÄ: ÓÇÂÍÙËâ 1,3-ÑÍÔÂÊËÐËÇ- N
ÄÞØ ÔÑÎÇÌ Ô ÂÊËÆÑÏ ÐÂÕÓËâ,130 ÃÇÐÊÑÕÓËÂÊÑÎÂ Ô ÅÎËÑÍÔÂÎÇÏ Ë
ÂÊËÆÑÏ ÐÂÕÓËâ,131 Â ÕÂÍÉÇ ÆËÂÊÑÕËÓÑÄÂÐËÇ 3-ÂÏËÐÑ-4-ÂÊËÆÑ-
1,2,5-ÑÍÔÂÆËÂÊÑÎÂ.132
7. ³ÑÎË ÕÇÕÓÂÊÑÎËâ
N3 C C NH2 NaNO2 NC C NO7Na+ ªÊÄÇÔÕÐÞ ËÊÑÏÇÓÐÞÇ 1,2,5-, 1,3,5-, 1,4,5- Ë 2,3,5-ÕÓËÊÂÏÇÜÇÐ-
N N CH3COOH N N ÐÞÇ ÔÑÎË ÕÇÕÓÂÊÑÎËâ. ®ÇÕÑÆÂÏ ÒÑÎÖÚÇÐËâ àÕËØ ÔÑÇÆËÐÇÐËÌ
O N ÃÞÎ ÒÑÔÄâÜÇÐ ÑÃÊÑÓ 136. ¯ËÉÇ ÓÂÔÔÏÂÕÓËÄÂáÕÔâ ÓÂÃÑÕÞ,
ÑÒÖÃÎËÍÑÄÂÐÐÞÇ ÒÑÔÎÇ 1986 Å. °ÒËÔÂÐÑ 137, 138 ÒÑÎÖÚÇÐËÇ
ÔÇÓËË 1,2,5-ÕÓËÊÂÏÇÜÇÐÐÞØ ÔÑÎÇÌ ÕÇÕÓÂÊÑÎËâ ÑÍËÔÎÇÐËÇÏ
1-(2-ÒËÓËÆËÎ)-3-ÂÓËÎÕÓËÂÊÇÐÑÄ 2,4,4,6-ÕÇÕÓÂÃÓÑÏÙËÍÎÑÅÇÍ-
6. 2,5-¥ËÊÂÏÇÜÇÐÐÞÇ ÕÇÕÓÂÊÑÎÞ
ÔÂ-2,5-ÆËÇÐ-1-ÑÐÑÏ.
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O
ÐÇÆÑÔÕÂÕÑÚÐÑ. ©Â ÒÑÔÎÇÆÐÇÇ ÆÇÔâÕËÎÇÕËÇ ÐÇ ÃÞÎÑ ÒÓÇÆÎÑÉÇÐÑ
ÐË ÑÆÐÑÅÑ ÒÓËÐÙËÒËÂÎßÐÑ ÐÑÄÑÅÑ ÔÒÑÔÑàÒÑÎÖÚÇÐËâ ÖÍÂÊÂÐ-
Br Br
ÐÞØ ÔÑÇÆËÐÇÐËÌ, ËÏÇáÜÇÅÑ ÑÃÜËÌ ØÂÓÂÍÕÇÓ. ´ÇÏ ÐÇ ÏÇÐÇÇ N N NHAr +
ÊÂÔÎÖÉËÄÂÇÕ ÖÒÑÏËÐÂÐËâ ÓÇÂÍÙËâ ËÏËÆÑËÎØÎÑÓËÆÑÄ Ô N
×ÇÐËÎÅËÆÓÂÊËÐÑÏ.133 Br Br

p-RC6H4C NNHSO2 + C6H5NHNH2

N 7
Cl Br
N+ N
N
Ar
p-RC6H4C N
N NC6H5
N ¡ÎÍËÎËÓÑÄÂÐËÇ 1,5- Ë 2,5-ÆËÊÂÏÇÜÇÐÐÞØ ÕÇÕÓÂÊÑÎÑÄ
âÄÎâÇÕÔâ ÖÆÑÃÐÞÏ ÏÇÕÑÆÑÏ ÔËÐÕÇÊ ÔÑÎÇÌ ÕÇÕÓÂÊÑÎËâ.136
R = H, CH3, OCH3, NO2 ¯ÇÆÂÄÐÑ ÒÑÍÂÊÂÐÑ,139 ÚÕÑ ÒÓË ÂÎÍËÎËÓÑÄÂÐËË 1,5-ÆËÊÂÏÇÜÇÐ-
ÐÞØ ÕÇÕÓÂÊÑÎÑÄ ÆËÂÎÍËÎÔÖÎß×ÂÕÂÏË ËÎË ÂÎÍËÎËÑÆËÆÂÏË Ô
ØÑÓÑÛËÏ ÄÞØÑÆÑÏ ÑÃÓÂÊÖáÕÔâ 1,4,5-ÕÓËÊÂÏÇÜÇÐÐÞÇ ÔÑÎË
¥Îâ ÔËÐÕÇÊ ËÏËÆÑËÎØÎÑÓËÆÑÄ ÃÞÎË ËÔÒÑÎßÊÑÄÂÐÞ N-ÐÂ×- ÕÇÕÓÂÊÑÎËâ. µÍÂÊÂÐÐÞÇ ÔÑÎË ÕÇÕÓÂÊÑÎËâ ÃÞÎË ÕÂÍÉÇ ÒÑÎÖ-
ÕËÎÔÖÎß×ÑÐËÎÃÇÐÊÅËÆÓÂÊËÆÞ. ÚÇÐÞ ÒÓË ÒÑÔÎÇÆÑÄÂÕÇÎßÐÑÌ ÑÃÓÂÃÑÕÍÇ ÐËÕÓËÎÑÄ ÏÇÕËÎÑÄÞÏ
°ÓËÅËÐÂÎßÐÞÌ ÏÇÕÑÆ ÒÑÎÖÚÇÐËâ 2-ÂÓËÎ-5-(2-ÂÓËÎÕÇÕÓÂ- à×ËÓÑÏ ÕÓË×ÕÑÓÏÇÕÂÐÔÖÎß×ÑÍËÔÎÑÕÞ Ë ÏÇÕËÎÂÊËÆÑÏ.140
ÊÑÎ-5-ËÎ)ÕÇÕÓÂÊÑÎÑÄ, ÑÔÐÑÄÂÐÐÞÌ ÐÂ ÓÇÂÍÙËË ÃËÔÂÓËÎÅËÆÓÂ- F3CSO3CH3 +
CH3N3
ÊÑÐÑÄ ÅÎËÑÍÔÂÎâ Ô 2,4,6-ÕÓËÃÓÑÏÂÊËÆÑÃÇÐÊÑÎÑÏ, ÒÓÇÆÎÑÉËÎË R2HCCN R2HC C N CH3 F3CSOÿ
3
ÂÄÕÑÓÞ ÓÂÃÑÕÞ 134 (ÔØÇÏÂ 1).
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ÜÇÐËâ ÍÑÐÆÇÐÔËÓÑÄÂÐÐÑÅÑ 2-×ÇÐËÎ-4-ÂÏËÐÑ-1,2,3-ÕÓË-
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C
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3
CH3 N
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×ÂÊ.34, 141, 142
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ÕÂØ 143 ë 145.
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ËÔÒÑÎßÊÑÄÂÎÔâ ÏÇÕÑÆ ab initio. £ ÃÂÊËÔÂØ 6-31G** Ë
6.311+G(2d,2p) ÄÞÚËÔÎÇРÒÑÎÐÂâ àÐÇÓÅËâ 1H- Ë 2¯-ÕÂÖÕÑ-
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ÔÒÇÍÕÓÑÄ.149, 150 ¯ÂÒÓÑÕËÄ, ÓÂÔÚÇÕÞ ÔÑÄÓÇÏÇÐÐÞÏ ÒÑÎÖàÏÒË-
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5-×ÕÑÓÕÇÕÓÂÊÑÎÂ.36, 37
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6-31G**/6-31G.38, 151 ¡ÐÂÎÑÅËÚÐÞÌ ÂÐÂÎËÊ ÒÓÑÄÇÆÇÐ ÆÎâ ÒÓÑ-
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ÔÑÅÎÂÔÐÑ ÓÂÔÚÇÕÂÏ ab initio (6-31G), ÙÇÐÕÓÑÏ ÑÔÐÑÄÐÑÔÕË
ÕÂÍÉÇ âÄÎâÇÕÔâ ÂÕÑÏ N(4) ÅÇÕÇÓÑÙËÍÎÂ.152
ºËÓÑÍÑÇ ÒÓËÏÇÐÇÐËÇ ÍÄÂÐÕÑÄÑØËÏËÚÇÔÍËØ ÏÇÕÑÆÑÄ
ÒÑÊÄÑÎËÎÑ ÒÑÎÖÚËÕß ÙÇÐÐÖá ËÐ×ÑÓÏÂÙËá ÐÇ ÕÑÎßÍÑ Ñ ÒÓÑ-
ÕÑÕÓÑÒÐÑÌ ÕÂÖÕÑÏÇÓËË ÕÇÕÓÂÊÑÎÑÄ, ÐÑ Ë ÒÑ ÏÐÑÅËÏ ÆÓÖÅËÏ
ËÐÕÇÓÇÔÐÞÏ ÄÑÒÓÑÔÂÏ. ´ÂÍ, ÏÇÕÑÆÑÏ ab initio ÒÓÑÄÇÆÇÐ
ÕÑÒÑÎÑÅËÚÇÔÍËÌ ÂÐÂÎËÊ ÔÕÓÑÇÐËâ ÍÑÏÒÎÇÍÔÑÄ ÕÇÕÓÂÊÑÎÂ Ô
Li+, Na+, K+ Ë Al3+. ±ÑÍÂÊÂРÄÑÊÏÑÉÐÑÔÕß ÓÂÊÎËÚÐÑÅÑ
ÄÊÂËÏÐÑÅÑ ÓÂÔÒÑÎÑÉÇÐËâ Ä ÒÓÑÔÕÓÂÐÔÕÄÇ ÅÇÕÇÓÑÙËÍÎËÚÇÔ-
ÍÑÅÑ ÎËÅÂÐÆÂ Ë ËÑÐÂ ÏÇÕÂÎÎÂ.40
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ÒÓÑËÊÄÑÆÐÞØ Ô ÖÔÒÇØÑÏ ÒÓËÄÎÇÍÂáÕÔâ Ë ÔÑÄÓÇÏÇÐÐÞÇ
ÒÑÎÖàÏÒËÓËÚÇÔÍËÇ ÏÇÕÑÆÞ. ±ÑÍÂÊÂÐÑ, ÚÕÑ ÏÇÕÑÆ MNDO
ÂÆÇÍÄÂÕÐÑ ÑÒËÔÞÄÂÇÕ àÎÇÍÕÓÑÐÐÖá ÔÕÓÖÍÕÖÓÖ ÕÇÕÓÂÊÑÎÑÄ,
ÒÓËÚÇÏ ÒÓËÏÇÐÇÐËÇ àÕÑÅÑ ÏÇÕÑÆÂ ËÐÑÅÆÂ ÑÍÂÊÞÄÂÇÕÔâ ÃÑÎÇÇ
ÒÓÇÆÒÑÚÕËÕÇÎßÐÞÏ, ÚÇÏ ËÔÒÑÎßÊÑÄÂÐËÇ ÏÇÕÑÆ ab initio Ä
ÏËÐËÏÂÎßÐÑÏ ÃÂÊËÔÇ.153 £ÏÇÔÕÇ Ô ÕÇÏ ÑÕÏÇÚÂÇÕÔâ, ÚÕÑ àÕÑÕ
ÏÇÕÑÆ ÆÂÇÕ ÊÂÐËÉÇÐÐÞÇ Ð 83.8 괃 . ÏÑÎß71 ÊÐÂÚÇÐËâ àÐ-
ÕÂÎßÒËË ÑÃÓÂÊÑÄÂÐËâ: 230.5 Ë 248.0 괃 . ÏÑÎß71 ÆÎâ 1H- Ë
2¯-ÕÇÕÓÂÊÑÎÑÄ ÔÑÑÕÄÇÕÔÕÄÇÐÐÑ.36
¤.ª.¬ÑÎÆÑÃÔÍËÌ, £.¡.°ÔÕÓÑÄÔÍËÌ
±ÇÓÇÚËÔÎËÏ ÇÜÇ ÐÇÔÍÑÎßÍÑ ÓÂÃÑÕ, Ä ÍÑÕÑÓÞØ ËÔÔÎÇÆÑÄÂ-
ÎÑÔß àÎÇÍÕÓÑÐÐÑÇ ÔÕÓÑÇÐËÇ ÕÇÕÓÂÊÑÎÑÄ. ´ÂÍ, Ä ÓÂÃÑÕÂØ 154, 155
ËÊÖÚÇРàÎÇÍÕÓÑÐÐÂâ ÔÕÓÖÍÕÖÓ ÓÂÊÎËÚÐÞØ ÂÎÍËÎ- Ë ÂÎÍÇÐËÎ-
ÒÓÑËÊÄÑÆÐÞØ ÕÇÕÓÂÊÑÎÂ (MNDO), Ä ÓÂÃÑÕÇ 156 ÄÞÚËÔÎÇÐÞ
ÊÐÂÚÇÐËâ ÔÓÑÆÔÕÄÂ Í ÒÓÑÕÑÐÖ ÕÇÕÓÂÊÑÎÂ Ë ÊÂÏÇÜÇÐÐÞØ ÕÇÕÓÂ-
ÊÑÎÑÄ, Ä ÓÂÃÑÕÇ 36 ÄÞÒÑÎÐÇÐ ÂÐÂÎËÊ ÂÊËÆÑÂÊÑÏÇÕËÐ-ÕÇÕÓÂ-
ÊÑÎßÐÑÅÑ ÓÂÄÐÑÄÇÔËâ, Â Ä ÓÂÃÑÕÇ 157 ÓÂÔÔÏÂÕÓËÄÂÇÕÔâ
ÔÕÓÑÇÐËÇ ÃËÒÑÎâÓÐÑÅÑ ÕÇÕÓÂÊÑÎÂÕÆËÂÊÑÐËâ. ³áÆ ÉÇ ÔÎÇ-
ÆÖÇÕ ÑÕÐÇÔÕË ÐÇÆÂÄÐÑ ÑÒÖÃÎËÍÑÄÂÐÐÞÇ ÓÇÊÖÎßÕÂÕÞ ÓÂÔÚÇÕÂ
(ab initio) ÒÓÑ×ËÎâ ÒÑÕÇÐÙËÂÎßÐÑÌ àÐÇÓÅËË ÒÇÓÇÅÓÖÒÒËÓÑÄÍË
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ÔÕË ÏÂÎÑÔÕÂÃËÎßÐÞØ àÎÇÍÕÓÑÐÐÞØ ÔÑÔÕÑâÐËÌ ÕÇÕÓÂÊÑÎÂ, 159 Â
ÕÂÍÉÇ ÓÇÊÖÎßÕÂÕÞ ÒÑÎÖàÏÒËÓËÚÇÔÍËØ ÓÂÔÚÇÕÑÄ àÎÇÍÕÓÑÐÐÞØ
ÒÂÓÂÏÇÕÓÑÄ ÓÇÂÅÇÐÕÑÄ Ë ÒÓÑÆÖÍÕÑÄ ÓÇÂÍÙËÌ ÂÎÍËÎËÓÑÄÂÐËâ
ÔÑÎÇÌ 5-ÊÂÏÇÜÇÐÐÞØ ÕÇÕÓÂÊÑÎÑÄ (CNDO, CNDO/2),160, 161
ËÔÚÇÓÒÞÄÂáÜÇÅÑ ÂÎÍËÎËÓÑÄÂÐËâ ËÊÑÏÇÓÐÞØ N-ÂÎÍËÎÕÇÕÓÂ-
ÊÑÎÑÄ 162 Ë ÂÏËÐÑÏÇÕËÎËÓÑÄÂÐËâ N-ÂÎÍËÎ-5-ÂÏËÐÑÕÇÕÓÂÊÑ-
ÎÑÄ (CNDO/2).163
¬ÄÂÐÕÑÄÑØËÏËÚÇÔÍËÇ ÓÂÔÚÇÕÞ à××ÇÍÕËÄÐÑ ËÔÒÑÎßÊÖáÕÔâ
ÆÎâ ËÐÕÇÓÒÓÇÕÂÙËË µ¶-ÔÒÇÍÕÓÑÄ 1,4-ÆËÅËÆÓÑ-5H-ÕÇÕÓÂÊÑÎÑÄ
(CNDO/S-CI),164 ÔÒÇÍÕÓÑÄ Á®² 15N ÕÇÕÓÂÊÑΠ(MNDO),
N-ÂÎÍËÎÕÇÕÓÂÊÑÎÑÄ (INDO/S-SOS),165, 166 N-ÂÏËÐÑÕÇÕÓÂÊÑ-
ÎÑÄ (INDO),167, 168 ÕÇÕÓÂÊÑÎÑÒËÓËÆËÐÑÄ (INDO/S-SOS),169 Â
ÕÂÍÉÇ ÏÂÔÔ-ÔÒÇÍÕÓÑÄ ËÊÑÏÇÓÐÞØ ÏÇÕËÎÕÇÕÓÂÊÑÎÑÄ (CNDO,
CNDO/2).150, 170
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2. ¿ÎÇÍÕÓÑÐÐÞÇ, ×ÑÕÑàÎÇÍÕÓÑÐÐÞÇ Ë ÍÑÎÇÃÂÕÇÎßÐÞÇ
ÔÒÇÍÕÓÞ
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ÓÂÃÑÕÞ ÒÑ ÒÓËÏÇÐÇÐËá µ¶-ÔÒÇÍÕÓÑÔÍÑÒËË ÍÂÍ ÂÐÂÎËÕËÚÇÔ-
ÍÑÅÑ ÏÇÕÑÆÂ ÒÓË ËÊÖÚÇÐËË ÒÓÑÕÑÎËÕËÚÇÔÍËØ ÓÂÄÐÑÄÇÔËÌ,
ÓÇÂÍÙËÑÐÐÑÌ ÔÒÑÔÑÃÐÑÔÕË, ÔÑÔÕÂÄÂ ÏÐÑÅÑÍÑÏÒÑÐÇÐÕÐÞØ ÔÏÇ-
ÔÇÌ ÕÇÕÓÂÊÑÎÑÄ. ´ÂÍ, ÏÇÕÑÆ µ¶-ÔÒÇÍÕÓÑÔÍÑÒËË ÃÞÎ Ô ÖÔÒÇØÑÏ
ËÔÒÑÎßÊÑÄÂÐ ÒÓË ÑÒÓÇÆÇÎÇÐËË ÍÑÐÔÕÂÐÕ ÍËÔÎÑÕÐÑÔÕË Ë ÑÔÐÑÄ-
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ÔÕË Ë ÓÇÅËÑÔÇÎÇÍÕËÄÐÑÔÕË ÓÇÂÍÙËÌ ÕÇÕÓÂÊÑÎÂÕ-ÂÐËÑÐÑÄ Ô
ÆËÏÇÕËÎÔÖÎß×ÂÕÑÏ,172, 173 àÕËÎÑÄÞÏ à×ËÓÑÏ ÃÓÑÏÖÍÔÖÔÐÑÌ
ÍËÔÎÑÕÞ 174 Ë ÏÇÕËÎÄËÐËÎÍÇÕÑÐÑÏ,175, 176 Â ÕÂÍÉÇ ÒÓË ËÊÖÚÇ-
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ÔÒÇÍÕÓÑÄ ÕÇÕÓÂÊÑÎÂÕ-ÂÐËÑÐÑÄ Í ÆÑÃÂÄÍÂÏ ÐÇÃÑÎßÛËØ ÍÑÎË-
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ÔÑÎßÄÂÕËÓÑÄÂÐÐÞØ ÕÇÕÓÂÊÑÎßÐÞØ ÔÖÃÔÕÓÂÕÑÄ.173
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Ä ÓÂÃÑÕÇ 177.
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ÊÑÎÑÄ, ÃÎÂÅÑÆÂÓâ ÒÑÄÞÛÇÐÐÑÌ ÔÕÂÃËÎËÊÂÙËË p-ÖÓÑÄÐÇÌ.178
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µÔÒÇØË ØËÏËË 63 (10) 1994
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ÃÖÕËÎÑÄÞÏ, ËÊÑÒÓÑÒËÎÑÄÞÏ ËÎË ÙËÍÎÑÅÇÍÔËÎÑÄÞÏ ÔÒËÓÕÑÏ
Ä 96%-ÐÑÌ ÔÇÓÐÑÌ ÍËÔÎÑÕÇ ÐÇÊÂÄËÔËÏÑ ÑÕ ÒÓËÓÑÆÞ ÊÂÏÇÔÕË-
ÕÇÎâ Ä ÒÑÎÑÉÇÐËË 5 ÕÇÕÓÂÊÑÎßÐÑÅÑ ÙËÍΠÑÃÓÂÊÖáÕÔâ ËÔÍÎá-
ÚËÕÇÎßÐÑ 2-ÊÂÏÇÜÇÐÐÞÇ ÕÇÕÓÂÊÑÎÞ.262 ³ÎÇÆÑÄÂÕÇÎßÐÑ,
ÔÇÎÇÍÕËÄÐÑÔÕß ÂÎÍËÎËÓÑÄÂÐËâ ÕÇÕÓÂÊÑÎÑÄ ÊÂÄËÔËÕ ÕÂÍÉÇ ÑÕ
ÕÑÅÑ, Ä ÍÂÍÑÌ ×ÑÓÏÇ ì ÐÇÌÕÓÂÎßÐÑÌ ËÎË ËÑÐËÊÑÄÂÐÐÑÌ ì
ÔÖÃÔÕÓÂÕ ÄÔÕÖÒÂÇÕ Ä ÓÇÂÍÙËá Ô ÂÎÍËÎËÓÖáÜËÏ ÂÅÇÐÕÑÏ.
£ÞÔÑÍÂâ ÔÇÎÇÍÕËÄÐÑÔÕß ÂÎÍËÎËÓÑÄÂÐËâ ÕÓËàÕËÎÂÏÏÑÐËÇÄÞØ
ÔÑÎÇÌ 5-ÂÓËÎÕÇÕÓÂÊÑÎÑÄ ÏÇÕËÎÄËÐËÎÍÇÕÑÐÑÏ Ä ÂÒÓÑÕÑÐÐÞØ
ÆËÒÑÎâÓÐÞØ ÓÂÔÕÄÑÓËÕÇÎâØ (ÑÃÓÂÊÖáÕÔâ ÕÑÎßÍÑ ÔÑÑÕÄÇÕ-
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ÒÓÑÔÕÓÂÐÔÕÄÇÐÐÞÏ ÃÎÑÍËÓÑÄÂÐËÇÏ ÂÕÑÏÂ N(1) ÕÇÕÓÂÊÑÎß-
ÐÑÅÑ ÙËÍÎÂ.175, 176
±ÓË ÂÎÍËÎËÓÑÄÂÐËË ÕÇÕÓÂÊÑÎÑÄ Ä ÖÔÎÑÄËâØ ÏÇÉ×ÂÊÐÑÅÑ
ÍÂÕÂÎËÊÂ Ë Ä ÅÑÏÑÅÇÐÐÞØ ÔÓÇÆÂØ ÊÂÏÇÕÐÞØ ÑÕÎËÚËÌ Ä ÔÇÎÇÍ-
ÕËÄÐÑÔÕË ÓÇÂÍÙËÌ ÐÇ ÄÞâÄÎÇÐÑ.162 £ ÕÑ ÉÇ ÄÓÇÏâ Ä ÒÓÇÒÂÓÂ-
ÕËÄÐÑÏ ÑÕÐÑÛÇÐËË ÂÎÍËÎËÓÑÄÂÐËÇ Ô ÒÓËÏÇÐÇÐËÇÏ
ÏÇÉ×ÂÊÐÑÅÑ ÍÂÕÂÎËÊ ì ÄÇÔßÏ ÒÇÓÔÒÇÍÕËÄÐÞÌ ÏÇÕÑÆ, ÒÑÊÄÑ-
ÎâáÜËÌ Ä ÏâÅÍËØ ÖÔÎÑÄËâØ Ë Ô ÄÞÔÑÍËÏ ÄÞØÑÆÑÏ, ËÔÒÑÎßÊÖâ
ÒÓÑÔÕÞÇ Ë ÆÑÔÕÖÒÐÞÇ ÓÇÂÅÇÐÕÞ Ë ÓÂÔÕÄÑÓËÕÇÎË, ÒÑÎÖÚÂÕß
ÓÂÊÐÑÑÃÓÂÊÐÞÇ N-ÏÑÐÑ- Ë N,N0 -ÆËÊÂÏÇÜÇÐÐÞÇ ÕÇÕÓÂÊÑÎÞ.270
4. ¡ÙËÎËÓÑÄÂÐËÇ Ë ËÏËÆÑËÎËÓÑÄÂÐËÇ
²ÇÂÍÙËË ÕÇÕÓÂÊÑÎÑÄ Ô ÂÙËÎËÓÖáÜËÏË ÓÇÂÅÇÐÕÂÏË Ë ËÏË-
ÆÑËÎØÎÑÓËÆÂÏË Ä ÒÑÔÎÇÆÐËÇ ÐÇÔÍÑÎßÍÑ ÎÇÕ ÒÓËÑÃÓÇÎË ÑÔÑ-
ÃÑÇ ÊÐÂÚÇÐËÇ, ÅÎÂÄÐÞÏ ÑÃÓÂÊÑÏ Ä ÔÄâÊË Ô ÕÇÏ, ÚÕÑ Ô ËØ
ÒÑÏÑÜßá ÏÑÅÖÕ ÃÞÕß ÒÑÎÖÚÇÐÞ 2,5-ÆËÊÂÏÇÜÇÐÐÞÇ 1,3,4-
855
ÑÍÔÂÆËÂÊÑÎÞ ÓÂÊÎËÚÐÑÅÑ ÔÕÓÑÇÐËâ,142, 247, 270 ë 273 Â ÕÂÍÉÇ
ÓÂÐÇÇ ÐÇÆÑÔÕÖÒÐÞÇ 3¯-1,3,4-ÃÇÐÊÑÕÓËÂÊÇÒËÐÞ.274 ë 277 ´ÂÍ,
ÕÇÕÓÂÊÑÎ Ë 5-ÊÂÏÇÜÇÐÐÞÇ ÕÇÕÓÂÊÑÎÞ ÒÓË ÂÙËÎËÓÑÄÂÐËË ØÎÑÓ-
ÂÐÅËÆÓËÆÂÏË ÑÓÅÂÐËÚÇÔÍËØ ÍËÔÎÑÕ Ä ÒÓËÔÖÕÔÕÄËË ÑÓÅÂÐËÚÇÔ-
ÍËØ ÑÔÐÑÄÂÐËÌ ÒÓË 100 ë 1208³ Ô ÄÞÔÑÍËÏ ÄÞØÑÆÑÏ
ÒÓÇÄÓÂÜÂáÕÔâ Ä ÔÑÑÕÄÇÕÔÕÄÖáÜËÇ 1,3,4-ÑÍÔÂÆËÂÊÑÎÞ.
R1C NH N N
C5H5N
N N + R2COCl
7N2 R1C CR2
N O
²ÂÐÇÇ ÒÑÎÂÅÂÎË, ÚÕÑ Ä àÕÑÌ ÓÇÂÍÙËË Ð ÒÇÓÄÑÌ ÔÕÂÆËË
ÑÃÓÂÊÖÇÕÔâ ÐÇÖÔÕÑÌÚËÄÞÌ 2-ÂÙËÎÕÇÕÓÂÊÑÎ, ÓÂÔÜÇÒÎÇÐËÇ
ÍÑÕÑÓÑÅÑ Ô ÄÞÆÇÎÇÐËÇÏ ÏÑÎÇÍÖÎÞ ÂÊÑÕÂ ÒÓËÄÑÆËÕ Í 1,3,4-
ÑÍÔÂÆËÂÊÑÎÖ.278 °ÆÐÂÍÑ Ä ÆÂÎßÐÇÌÛÇÏ, ÃÎÂÅÑÆÂÓâ ÒÓËÏÇÐÇ-
ÐËá ÏÇÉ×ÂÊÐÑÅÑ ÍÂÕÂÎËÊÂ, ÃÞÎÑ ÒÑÍÂÊÂÐÑ, ÚÕÑ ÒÓË ÂÙËÎËÓÑ-
ÄÂÐËË 5-ÂÓËÎÕÇÕÓÂÊÑÎÑÄ ØÎÑÓÂÐÅËÆÓËÆÂÏË ÊÂÏÇÜÇÐÐÞØ
ÃÇÐÊÑÌÐÞØ ÍËÔÎÑÕ ÒÑÎÖÚÂáÕÔâ ÐÇ ÕÑÎßÍÑ 2-ÃÇÐÊÑËÎÕÇÕÓÂ-
ÊÑÎÞ, ÐÑ Ë ËÊÑÏÇÓÐÞÇ 1-ÃÇÐÊÑËÎÕÇÕÓÂÊÑÎÞ.247, 271
ArC NH
CH2Cl27ÄÑÆÐ.NaOH,
+ R1C6H4COCl
N N +
1 ÏÂÔ.% (C4H9)4N Br7
N
ArC NCOC6H4R1 ArC N
N N + N NCOC6H4R1
N N
N
°ÃÓÂÊÑÄÂÐËá ÑÍÔÂÆËÂÊÑÎÑÄ ËÊ 1-ÃÇÐÊÑËÎÕÇÕÓÂÊÑÎÑÄ
NR2
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ÜÇÒÎÇÐËâ Ë àÎËÏËÐËÓÑÄÂÐËâ ÏÑÎÇÍÖÎÞ ÂÊÑÕ 2-ÃÇÐ-
ÊÑËÎÕÇÕÓÂÊÑÎ ÒÓÇÄÓÂÜÂÇÕÔâ Ä ÂÙËÎÐËÕÓËÎËÏËÐ, ÙËÍÎËÊÂÙËâ
ÍÑÕÑÓÑÅÑ ÒÓËÄÑÆËÕ Í ÑÍÔÂÆËÂÊÑÎÖ.
£ ÒÓÂÍÕËÚÇÔÍÑÏ ÑÕÐÑÛÇÐËË ÐÂËÃÑÎßÛËÌ ËÐÕÇÓÇÔ ÒÓÇÆ-
ÔÕÂÄÎâáÕ ÓÇÊÖÎßÕÂÕÞ, ÒÑÎÖÚÇÐÐÞÇ ÒÓË ËÊÖÚÇÐËË ÂÙËÎËÓÑÄÂ-
ÐËâ 5-ÊÂÏÇÜÇÐÐÞØ ÕÇÕÓÂÊÑÎÑÄ ÂÐÅËÆÓËÆÂÏË ÍÂÓÃÑÐÑÄÞØ
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ÐÂËÃÑÎÇÇ à××ÇÍÕËÄÐÞØ Ë ÒÓÑÔÕÞØ ÏÇÕÑÆÑÄ ÒÑÎÖÚÇÐËâ 2(5)-
ÏÑÐÑ- Ë 2,5-ÆËÊÂÏÇÜÇÐÐÞØ 1,3,5-ÑÍÔÂÆËÂÊÑÎÑÄ.
£ ÕÇÚÇÐËÇ ÒÑÔÎÇÆÐËØ ÕÓËÆÙÂÕË ÎÇÕ ÃÞÎÑ ÒÓËÐâÕÑ ÔÚËÕÂÕß,
ÚÕÑ ÓÇÂÍÙËâ 5-ÊÂÏÇÜÇÐÐÞØ ÕÇÕÓÂÊÑÎÑÄ Ô ËÏËÆÑËÎØÎÑÓËÆÂÏË,
ÒÓËÄÑÆâÜÂâ Í 3,4,5-ÕÓËÊÂÏÇÜÇÐÐÞÏ 1,2,4-ÕÓËÂÊÑÎÂÏ, ÒÓÑÕÇ-
ÍÂÇÕ ÒÑ ÏÇØÂÐËÊÏÖ, ÂÐÂÎÑÅËÚÐÑÏÖ ÏÇØÂÐËÊÏÖ ÂÙËÎËÓÑÄÂ-
ÐËâ.279 ±ÑÎÂÅÂÎË, ÚÕÑ ÒÓË ÐÂÅÓÇÄÂÐËË 5-ÊÂÏÇÜÇÐÐÞØ
ÕÇÕÓÂÊÑÎÑÄ Ô ËÏËÆÑËÎØÎÑÓËÆÂÏË Ä ÒËÓËÆËÐÇ, ÒÇÓÄÑÐÂÚÂÎß-
ÐÑ ÑÃÓÂÊÖÇÕÔâ ÐÇÖÔÕÑÌÚËÄÞÌ 2-ËÏËÆÑËÎÕÇÕÓÂÊÑÎ, ÍÑÕÑÓÞÌ Ä
ÓÇÊÖÎßÕÂÕÇ ÕÇÓÏËÚÇÔÍÑÅÑ ÓÂÔÜÇÒÎÇÐËâ Ë àÎËÏËÐËÓÑÄÂÐËâ
ÏÑÎÇÍÖÎÞ ÂÊÑÕÂ ÒÓÇÄÓÂÜÂÇÕÔâ Ä ËÏËÆÑËÎÐËÕÓËÎËÏËÐ.
±ÑÔÎÇÆÖáÜÂâ ÙËÍÎËÊÂÙËâ ËÏËÆÑËÎÐËÕÓËÎËÏËРÒÓËÄÑÆËÕ
Í 1,2,4-ÕÓËÂÊÑÎÖ. ±ÓË ËÊÖÚÇÐËË àÕÑÌ ÓÇÂÍÙËË Ä ÖÔÎÑÄËâØ
ÏÇÉ×ÂÊÐÑÅÑ ÍÂÕÂÎËÊ ÃÞÎÑ ÖÔÕÂÐÑÄÎÇÐÑ, ÚÕÑ Ð ÒÇÓÄÑÌ
ÔÕÂÆËË ÑÃÓÂÊÖÇÕÔâ ÐÇ ÕÑÎßÍÑ 2-ËÏËÆÑËÎÕÇÕÓÂÊÑÎ, ÐÑ Ë ËÊÑ-
ÏÇÓÐÞÌ 1-ËÏËÆÑËÎÕÇÕÓÂÊÑÎ. ±ÓËÐÙËÒËÂÎßÐÑ ÄÂÉÐÑ, ÚÕÑ ÒÓË
ÐÂÅÓÇÄÂÐËË ÒÑÎÖÚÇÐÐÞØ ÕÂÍËÏ ÔÒÑÔÑÃÑÏ ËÊÑÏÇÓÐÞØ ËÏË-
ÆÑËÎÕÇÕÓÂÊÑÎÑÄ Ä ÓÂÔÕÄÑÓÂØ ÕÑÎÖÑÎÂ, Ï-ÍÔËÎÑÎÂ ËÎË ÆËÑÍ-
ÔÂÐÂ, Â ÕÂÍÉÇ Ä ÑÕÔÖÕÔÕÄËÇ ÓÂÔÕÄÑÓËÕÇÎÇÌ, ÄÏÇÔÕÑ ÑÉËÆÂÇÏÞØ
3,4,5-ÕÓËÊÂÏÇÜÇÐÐÞØ 1,2,4-ÕÓËÂÊÑÎÑÄ ÑÃÓÂÊÖáÕÔâ ÓÂÐÇÇ
ÐÇËÊÄÇÔÕÐÞÇ 3¯-1,3,4-ÃÇÐÊÑÕÓËÂÊÇÒËÐÞ.276, 277
R1 C NH CH2Cl27ÄÑÆÐ.NaOH,
+ R2C NC6H5
N N +
N Cl 1 ÏÂÔ.% (C4H9)4N Br7
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R1C N CR2 R1 C N 2-ÂÎÍËÎ-5-ÂÏËÐÑÕÇÕÓÂÊÑÎÑÄ ÕÇÕÓÂÐËÕÓÑÏÇÕÂÐÑÏ Ä ÜÇÎÑÚÐÑÌ
D ÔÓÇÆÇ ÒÓËÄÑÆËÕ Í ÔÑÑÕÄÇÕÔÕÄÖáÜËÏ 5-ÐËÕÓÑÂÏËÐÑÕÇÕÓÂÊÑ-
N N NC6H5 + N N CR2
7N2
N N
NC6H5
ÎÂÏ.286, 287 ªÏÇáÕÔâ ÔÄÇÆÇÐËâ Ñ ÐËÕÓÑÄÂÐËË ÍÑÐÆÇÐÔËÓÑÄÂÐ-
R2
ÐÞØ ÔËÔÕÇÏ ì 5,6-ÆËÅËÆÓÑ-7¯-ËÏËÆÂÊÑÎÑ[1,2-d]ÕÇÕÓÂÊÑÎÂ,
7,8-ÆËÅËÆÓÑÕÇÕÓÂÊÑÎÑ[1,5-b]-1,2,4-ÕÓËÂÊËÐÂ Ë 5,6,7,8-ÕÇÕÓÂÅË-
N C ÆÓÑÕÇÕÓÂÊÑÎÑ[1,5-b]-1,2,4-ÕÓËÂÊËÐÂ,288 Â ÕÂÍÉÇ ÐÇÍÑÕÑÓÞØ
NH ÔÑÎÇÌ ÕÇÕÓÂÊÑÎËâ.289
±ÓË ÑÃÓÂÃÑÕÍÇ 5-ÂÏËÐÑÕÇÕÓÂÊÑΠÑÓÕÑà×ËÓÂÏË ÑÃÓÂ-
C N
ÊÖáÕÔâ ÔÑÑÕÄÇÕÔÕÄÖáÜËÇ ËÏËÐÑà×ËÓÞ,290  ÒÓË ÐÂÅÓÇÄÂÐËË
R1 Ô ÐËÕÓËÎÂÏË Ä ÒÓËÔÖÕÔÕÄËË ÑÓÅÂÐÑÃÑÓÂÐÑÄ ì ÂÏËÆËÐÞ.291
±ÑÆ ÆÇÌÔÕÄËÇÏ ØÎÑÓËÔÕÑÅÑ ÕËÑÐËΠ1-ÂÎÍËÎ-5-ÂÏËÐÑÕÇÕÓÂ-
ÊÑÎÞ ÐÇÑÉËÆÂÐÐÑ ÒÓÇÄÓÂÜÂáÕÔâ Ä 1,2,4-ÕËÂÆËÂÊÑÎÞ.292
5. ³ËÎËÎËÓÑÄÂÐËÇ, ×ÑÔ×ÑÓËÎËÓÑÄÂÐËÇ, ÔÖÎß×ÑÐËÓÑÄÂÐËÇ H2NC NCH2R N C N3
SOCl2
±ÓË ÄÊÂËÏÑÆÇÌÔÕÄËË ÐÂÕÓËÇÄÑÌ ÔÑÎË ÕÇÕÓÂÊÑÎÂ Ô ÕÓËÏÇÕËÎ- N N R C N
ØÎÑÓÔËÎÂÐÑÏ ÑÃÓÂÊÖÇÕÔâ ÕÓËÏÇÕËÎÔËÎËÎÕÇÕÓÂÊÑÎ Ô ÄÞØÑÆÑÏ N S
85%.47 ­ÖÚÛËÏ ÓÂÔÕÄÑÓËÕÇÎÇÏ ÆÎâ ÒÓÑÄÇÆÇÐËâ àÕÑÌ ÓÇÂÍÙËË
âÄÎâÇÕÔâ ØÎÑÓËÔÕÞÌ ÏÇÕËÎÇÐ, ÒÓÂÍÕËÚÇÔÍË ÐÇ ÒÓËÅÑÆÐÞ ÂÙÇ- °ÒËÔÂÐÑ ÂÙËÎËÓÑÄÂÐËÇ ÒÑ ÂÏËÐÑÅÓÖÒÒÇ 5-ÂÏËÐÑÕÇÕÓÂ-
ÕÑÐËÕÓËÎ Ë ¥®¶¡. ¡ÄÕÑÓÞ ÓÂÃÑÕÞ 47 ÐÇ ÑÃÔÖÉÆÂáÕ ÒÓÑ- ÊÑΠØÎÑÓÂÐÅËÆÓËÆÂÏË ÂÓÑÏÂÕËÚÇÔÍËØ ÍÂÓÃÑÐÑÄÞØ ÍËÔ-
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ËÔÍÎáÚËÕß ÄÑÊÏÑÉÐÑÔÕß ÑÃÓÂÊÑÄÂÐËâ ÆÄÖØ ËÊÑÏÇÓÑÄ ì 1- Ë Ò-ÙËÂÐÑ×ÇÐËÎÍÂÓÃÑÐËÎËÏËÆÑËÎØÎÑÓËÆÑÏ.295 £ ÒÑÔÎÇÆÐÇÏ
2-ÕÓËÏÇÕËÎÔËÎËÎÕÇÕÓÂÊÑÎÑÄ. µÆËÄËÕÇÎßÐÑ, ÚÕÑ ÒÓÑÃÎÇÏ ÔÎÖÚÂÇ ÓÇÂÍÙËâ ÕÂÍÉÇ ÒÓÑÕÇÍÂÇÕ ÒÑ àÍÊÑÙËÍÎËÚÇÔÍÑÌ ÂÏËÐÑ-
ÓÇÅËÑÔÇÎÇÍÕËÄÐÑÔÕË ÕÂÍÉÇ ÐÇ ÑÃÔÖÉÆÂÎÂÔß ÒÓË ËÊÖÚÇÐËË ÅÓÖÒÒÇ.
×ÑÔ×ÑÓËÎËÓÑÄÂÐËâ 279 Ë ÔÖÎß×ÑÐËÓÑÄÂÐËâ 280 ÕÇÕÓÂÊÑÎÂ. ³ÚË- ³ÑÎË 2-ÂÎÍËÎ-5-ÐËÕÓÑÂÏËÐÑÕÇÕÓÂÊÑÎÂ Ä ÏâÅÍËØ ÖÔÎÑÄËâØ
ÕÂÇÕÔâ, ÚÕÑ Ä ÓÇÊÖÎßÕÂÕÇ àÕËØ ÓÇÂÍÙËÌ ÑÃÓÂÊÖáÕÔâ ÕÑÎßÍÑ ÂÎÍËÎËÓÖáÕÔâ ÅÎËÙËÆÑÎÑÏ.296 ´ÇÕÓÂÊÑÎßÐÑÇ ÍÑÎßÙÑ Ä àÕÑÏ
1-ÊÂÏÇÜÇÐÐÞÇ ÕÇÕÓÂÊÑÎÞ. ÔÎÖÚÂÇ ÐÇ ÊÂÕÓÂÅËÄÂÇÕÔâ.
O
(C6H5O)2P(O)Cl, N(C2H5)3 NO2
HC N P(OC6H5)2 +
NH4 N C N
7
N N + H2 C CHCH2OH
HC NH N N N R
SO2Cl N O
N N N
N
, N(C2H5)3 HC N SO2
NO2
N N
N N HOCH2CH CH2 N C N
OH N N R
N

6. ¥ÇÌÔÕÄËÇ àÎÇÍÕÓÑ×ËÎßÐÞØ ÓÇÂÅÇÐÕÑÄ Ð ÊÂÏÇÜÇÐÐÞÇ 1,5-¥ËÂÏËÐÑÕÇÕÓÂÊÑÎ âÄÎâÇÕÔâ ËÐÕÇÓÇÔÐÞÏ ÓÇÂÅÇÐÕÑÏ Ä

ÔËÐÕÇÊÇ ÅÇÕÇÓÑÙËÍÎÑÄ ÓÂÊÎËÚÐÑÅÑ ÔÕÓÑÇÐËâ. ´ÂÍ, ÒÓË ÄÊÂËÏÑ-
ÕÇÕÓÂÊÑÎÞ
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N
2-ÏÇÕËÎ-5-ÄËÐËÎÕÇÕÓÂÊÑÎÂ Ô ÂÍÓËÎÑÐËÕÓËÎÑÏ Ä ÏÂÍÓÑÙÇÒË
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N (CH3)2CO ÏÇÓ ÊÐÂÚËÕÇÎßÐÑÌ ÆÎËÐÞ, ÚÕÑ ÔÄËÆÇÕÇÎßÔÕÄÖÇÕ Ñ ÔÍÎÑÐÐÑÔÕË
N ÄËÐËÎÕÇÕÓÂÊÑÎÂ Í ÅÑÏÑÒÑÎËÏÇÓËÊÂÙËË. £ ÕÑ ÉÇ ÄÓÇÏâ ÒÓË
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ÔÑÒÑÎËÏÇÓÂ ÄÞÛÇ.

H3C CH3 N N
11. ¶ÑÕÑØËÏËÚÇÔÍËÇ ÒÓÇÄÓÂÜÇÐËâ
H3C + N D
C N N ±ÓË ×ÑÕÑÎËÊÇ ÕÇÕÓÂÊÑÎÑÄ ÒÓÑËÔØÑÆËÕ ËØ ×ÓÂÅÏÇÐÕÂÙËâ Ô
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N N
7 ÙËÍÎËÚÇÔÍÑÌ ÔËÔÕÇÏÞ. ´ÂÍ, ËÊ 1,5-ÆËÂÓËÎÕÇÕÓÂÊÑÎÑÄ Ô ØÑÓÑ-
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Cl
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CH3 N N Cl
N hn
H3C N C N F
7N2
H3C N N N
N N N
H
Cl
N

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H Cl
1,2,3-ÕÓËÂÊÑÎ.140 ¡ÄÕÑÓÞ ÓÂÃÑÕÞ 140 ÔÚËÕÂáÕ, ÚÕÑ ÐÂ ÒÇÓÄÑÌ
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12. ¬ÑÏÒÎÇÍÔÞ ÕÇÕÓÂÊÑÎÑÄ Ô ÏÇÕÂÎÎÂÏË
ÐÞÇ 4,5-ÆËÅËÆÓÑÕÇÕÓÂÊÑÎ-5-ÑÐÞ.328 ë 330
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H
C N ÔÑÑÃÓÂÊÑÄÂÐËá ÔÑÑÕÄÇÕÔÕÄÖáÜËØ ÅÇÕÇÓÑÙËÍÎËÚÇÔÍËØ
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N N
N ÅÑÆÑÄ.335 ë 338 ¯ÇÊÂÏÇÜÇÐÐÞÌ ÕÇÕÓÂÊÑÎ ÎÇÅÍÑ ÑÃÓÂÊÖÇÕ ÍÑÏ-
R ÒÎÇÍÔÞ Ô ØÎÑÓËÆÂÏË Co(II), Ni(II), Cu(II) Ë Cd(II).335 ±ÑÍÂ-
ÊÂÐÑ ÕÂÍÉÇ, ÚÕÑ 1- Ë 2-ÏÑÐÑÂÎÍËÎÕÇÕÓÂÊÑÎÞ ÒÓË
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ÓËÄÂÕßÔâ ÍÂÍ ÏÇÕÑÆ ÒÑÎÖÚÇÐËâ ÕÓÖÆÐÑÆÑÔÕÖÒÐÞØ 1,2-ÆËÆÇ- ÑÃÓÂÊÖáÕÔâ ÍÑÏÒÎÇÍÔÞ ÑÃÜÇÌ ×ÑÓÏÖÎÞ Cu´2X2.339, 340 1- Ë
ÅËÆÓÑ-1,3-ÆËÂÊÇÒËÐÑÄ. 2-©ÂÏÇÜÇÐÐÞÇ ÕÇÕÓÂÊÑÎÞ âÄÎâáÕÔâ ÏÑÐÑÆÇÐÕÂÕÐÞÏË ÎËÅÂÐ-
ÆÂÏË, ÍÑÕÑÓÞÇ ÍÑÑÓÆËÐËÓÖáÕÔâ Ô ÙÇÐÕÓÂÎßÐÞÏ ÂÕÑÏÑÏ Cu
F3C F3C ÑÆÐËÏ ËÊ ÂÕÑÏÑÄ ÂÊÑÕÂ. ³ÖÜÇÔÕÄÇÐÐÑ, ÚÕÑ 1-ÂÎÍËÎÕÇÕÓÂÊÑÎÞ
hn
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7N2
N N N N3 ±ÑÆÓÑÃÐÑ ËÊÖÚÇÐÞ ÍÑÏÒÎÇÍÔÞ 5-ÊÂÏÇÜÇÐÐÞØ ÕÇÕÓÂÊÑÎÑÄ Ô
Co(II) Ë ³o(III).341 ë 343 ±ÑÍÂÊÂÐÑ, ÚÕÑ ÒÓË ÄÊÂËÏÑÆÇÌÔÕÄËË
N N 5-ÂÏËÐÑÕÇÕÓÂÊÑÎÂ Ô ÐËÕÓÂÕÑÏ ÒÇÐÕÂÂÏÏËÂÍÂÕÂ ÍÑÃÂÎßÕÂ
ÑÃÓÂÊÖÇÕÔâ ÍÑÏÒÎÇÍÔ ÔÑÔÕÂÄ [Co(NH3)5T](NO3)3.343 £ÊÂËÏÑ-
CF3 ÆÇÌÔÕÄËÇÏ ÂÊËÆÑÒÑÓ×ËÓËÐÑÄ Ô ÐËÕÓËÎÂÏË ÒÑÎÖÚÇÐÞ ÍÑÏ-
F3C
ÒÎÇÍÔÞ Ô In(III) Ë Fe(III) ÔÑÔÕÂÄÂ PMT, ÅÆÇ P ì ÆËÂÐËÑÐ
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N N: N N ÏÇÕÂÎÎÂ.344, 345 ±ÑÎÖÚÇÐÞ ÏÐÑÅÑÚËÔÎÇÐÐÞÇ ÍÑÏÒÎÇÍÔÞ 1,5-
ÆËÊÂÏÇÜÇÐÐÞØ ÕÇÕÓÂÊÑÎÑÄ Ô ØÎÑÓËÆÂÏË Co(II), Ni(II), Cu(II)
®ÇØÂÐËÊÏ ×ÑÕÑÎËÊ 2,5-ÆËÊÂÏÇÜÇÐÐÞØ ÕÇÕÓÂÊÑÎÑÄ ËÔÔÎÇ- Ë Fe(III). ±ÑÍÂÊÂÐÑ, ÚÕÑ ÒÓË ÄÊÂËÏÑÆÇÌÔÕÄËË 1,5-ÆËÊÂÏÇÜÇÐ-
ÆÑÄÂÐ Ä ÓÂÃÑÕÇ 332. ±ÑÍÂÊÂÐÑ, ÚÕÑ ËÐÕÇÓÏÇÆËÂÕÂÏË Ä àÕËØ ÐÞØ ÕÇÕÓÂÊÑÎÑÄ Ô CuCl2 Ä ÑÓÅÂÐËÚÇÔÍËØ ÓÂÔÕÄÑÓËÕÇÎâØ ÒÓË
ÓÇÂÍÙËâØ âÄÎâáÕÔâ ÔÑÑÕÄÇÕÔÕÄÖáÜËÇ ÐËÕÓËÎËÏËÐÞ. °ÃÓÂ- 25 ë 308³ Ô ÄÞÔÑÍËÏ ÄÞØÑÆÑÏ ÑÃÓÂÊÖáÕÔâ ÍÓËÔÕÂÎÎËÚÇÔÍËÇ
ÊÑÄÂÐËÇ ËÏËÐÑÂÊËÓËÆËÐÑÄ ÊÂ×ËÍÔËÓÑÄÂÐÑ ÒÓË ×ÑÕÑÎËÊÇ 4,5- ÍÑÏÒÎÇÍÔÞ ÔÑÔÕÂÄ CuTCl2.340 ®ÑÎÇÍÖÎÞ 1,5-ÆËÊÂÏÇÜÇÐÐÞØ
ÆËÅËÆÓÑ-5-ÂÎÍËÎËÆÇÐÕÇÕÓÂÊÑÎÑÄ.333 ÕÇÕÓÂÊÑÎÑÄ Ä ÕÂÍËØ ÍÑÏÒÎÇÍÔÂØ, ÒÑ-ÄËÆËÏÑÏÖ, âÄÎâáÕÔâ
ÏÑÔÕËÍÑÄÞÏË ÎËÅÂÐÆÂÏË. ¬ÂÉÆÂâ ÏÑÎÇÍÖΠÕÇÕÓÂÊÑÎßÐÑÅÑ
R1 R2 ÎËÅÂÐÆ ÔÄâÊÂРÑÆÐÑÄÓÇÏÇÐÐÑ Ô ÆÄÖÏâ ÔÑÔÇÆÐËÏË ËÑÐÂÏË
R2 Cu2+, ÔÑÇÆËÐÇÐÐÞÏË ÏÇÉÆÖ ÔÑÃÑÌ ÏÑÔÕËÍÑÄÞÏË ËÑÐÂÏË
C hn NCH3 ³l7. ¢ÂÓËÇÄÞÇ ÍÑÏÒÎÇÍÔÞ 1,5-ÆËÊÂÏÇÜÇÐÐÞØ ÕÇÕÓÂÊÑÎÑÄ
H3C N N CH3 7N2 R1 ÑÒËÔÂÐÞ Ä ÓÂÃÑÕÇ 346. ·ÑÓÑÛËÏË ÔËÆÇÓÑ×ÑÓÂÏË ÑÍÂÊÂÎËÔß
N
N N 1,5-ÆËÊÂÏÇÜÇÐÐÞÇ 4,5-ÆËÅËÆÓÑÕÇÕÓÂÊÑÎÞ.347, 348 ±ÓË ÑÃÓÂ-
CH3 ÃÑÕÍÇ ÏÇÕËÎÑÄÞØ à×ËÓÑÄ 2-(1-R-4,5-ÆËÅËÆÓÑÕÇÕÓÂÊÑÎ-5-
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ÎËÌØÎÑÓËÆÂ ËÊÖÚÇÐ Ä ÄÑÆÐÞØ ÓÂÔÕÄÑÓÂØ ÒÓË Ó¯ 9 ë 11.5 ÙÄÇÕÂ ÔÑÔÕÂÄÂ FeT3. £ ÕÂÍËØ ÍÑÏÒÎÇÍÔÂØ ÍÂÉÆÂâ ËÊ ÕÓÇØ
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ÙËË, ÄÍÎáÚÂáÜËÌ ÑÃÓÂÊÑÄÂÐËÇ ÒÓÑÏÇÉÖÕÑÚÐÑÅÑ ÕÇÕÓÂÊÑÎËÇ- ÐÞÏ ËÑÐÑÏ Fe3+ ÂÕÑÏÑÏ ÂÊÑÕ ÅÇÕÇÓÑÙËÍÎÂ Ë ÍÂÓÃÑÐËÎßÐÞÏ
ÄÑÅÑ ÓÂÆËÍÂÎÂ.334 ÂÕÑÏÑÏ ÍËÔÎÑÓÑÆÂ. ±ÓË ÊÂÏÇÐÇ ØÎÑÓÐÑÅÑ ÉÇÎÇÊÂ ÐÂ FeSO4
ÑÃÓÂÊÖÇÕÔâ ÍÑÏÒÎÇÍÔ ÒÑÎËÏÇÓÐÑÅÑ ÔÑÔÕÂÄÂ (FeT2)n.
C N N
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C
e7 . ÆËÊÂÏÇÜÇÐÐÞØ ÕÇÕÓÂÊÑÎÑÄ. ¯ÇÆÂÄÐÑ ÑÒËÔÂÐÞ ÍÑÏÒÎÇÍÔÞ
N + N N N 2-ÏÇÕËÎ-5-ÄËÐËÎÕÇÕÓÂÊÑÎÑÄ Ô ØÎÑÓËÆÂÏË Cr(III), Ni(II),
N 7e7 N Co(II) Ë Pd(II). ±ÑÍÂÊÂÐÑ, ÚÕÑ Ä ÕÂÍËØ ÍÑÏÒÎÇÍÔÂØ ËÑÐ
ÏÇÕÂÎΠÍÑÑÓÆËÐËÓÖÇÕÔâ Ô ÂÕÑÏÑÏ N(4) ÕÇÕÓÂÊÑÎßÐÑÅÑ
ÎËÅÂÐÆÂ.349, 350 ¬ÑÏÒÎÇÍÔÞ Hg(II) Ë Pd(II) Ô ÔÑÎâÏË ÕÇÕÓÂÊÑ-
ÎËâ ÑÒËÔÂÐÞ Ä ÓÂÃÑÕÂØ.351, 352

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C N C N ÜËÇ 3-×ÇÐËÎ-4-ÂÎÍÇÐËÎÒËÓÂÊÑÎÞ.282 ¶ÓÂÅÏÇÐÕÂÙËâ ÂÎÍÇÐËÎ-
N + N N N ÕÇÕÓÂÊÑÎÑÄ ÒÓÑËÔØÑÆËÕ ÒÓË ËØ ÐÂÅÓÇÄÂÐËË Ä 1,2-ÆË-
N N H ØÎÑÓÃÇÐÊÑÎÇ, ÄÞØÑÆ ÒËÓÂÊÑÎÑÄ ì 79 ë 98%.
C6H5C N
D + 7
N NCH CHR C6H5C N NCH CHR
7N2
N

C6H5C N
RHC N
C
H
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°ÕÏÇÚÂÇÕÔâ ÓÑÔÕ ÒÓÑËÊÄÑÆÔÕÄÂ ÕÇÕÓÂÊÑÎÑÄ Ä ÒÓÑÏÞÛÎÇÐÐÑ
ÓÂÊÄËÕÞØ ÔÕÓÂÐÂØ.
­ËÕÇÓÂÕÖÓÂ
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TETRAZOLES
G.I.Koldobskii, V.A.Ostrovskii
St.Petersburg State Institute of Technology,
26, Moskovskii Prosp., 198013 St.Petersburg, Russian Federation, Fax +7(812)110-6285
In the review new data on preparation, physicochemical properties and practical application of tetrazoles
have been systematised. Results of recent researches of elecronic structure, base-acid properties,
tautomerism, reactivity as well as thermal stability of tetrazoles have been discussed.
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Received 27th May 1993