Fused Imidazopyrazoles: Synthetic Strategies and Medicinal Applications

<table>Reagents: a, N<svg height="10.9665pt" id="M12" style="vertical-align:-0.2032003pt" version="1.1" viewbox="0 -10.7633 15.953 10.9665" width="15.953pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.0135,0,0,-0.0135,0,0)"><path d="M381 665C170 665 44 498 44 318C44 125 188 -15 369 -15C552 -15 703 117 703 333C703 534 550 665 381 665ZM359 629C491 629 601 517 601 306C601 114 502 21 390 21C249 21 146 158 146 346S248 629 359 629Z" id="g190-80"></path><glyph.data ascent="989" descent="-360" horiz-adv-x="747" vert-adv-y="747"></glyph.data></g><g transform="matrix(.0095,0,0,-0.0095,10.158,-5.984)"><path d="M556 236V289H337V504H275V289H56V236H275V-4H337V236H556Z" id="g54-36"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="611" vert-adv-y="611"></glyph.data></g></svg>; b, <svg height="12.0701pt" id="M13" style="vertical-align:-3.26378pt" version="1.1" viewbox="0 -8.80632 30.2734 12.0701" width="30.2734pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.0135,0,0,-0.0135,0,0)"><path d="M719 650H483V622C553 619 576 606 581 560C585 532 588 487 588 394V148H585L167 650H20V622C67 618 88 610 109 585C127 562 129 557 129 484V264C129 173 126 124 123 93C118 44 92 31 35 28V0H272V28C204 32 181 44 176 95C173 124 170 172 170 264V515H172L598 -9H629V394C629 487 631 532 635 563C639 606 663 619 719 622V650Z" id="g190-79"></path><glyph.data ascent="989" descent="-360" horiz-adv-x="743" vert-adv-y="743"></glyph.data></g><g transform="matrix(.0095,0,0,-0.0095,10.104,3.264)"><path d="M414 144C384 79 371 75 317 75H135L276 221C367 316 408 376 408 465C408 570 327 635 237 635C179 635 131 609 100 575L42 494L67 471C94 510 138 565 205 565C277 565 321 517 321 435C321 348 258 270 195 195C146 137 88 81 33 26V0H411C423 44 433 88 446 135L414 144Z" id="g50-51"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="487" vert-adv-y="487"></glyph.data></g><g transform="matrix(.0135,0,0,-0.0135,15.238,0)"><path d="M729 650H468V622C546 615 554 610 554 527V365H213V527C213 610 221 616 297 622V650H38V622C120 616 128 611 128 527V123C128 39 120 34 40 28V0H303V28C221 34 213 40 213 123V322H554V123C554 39 546 34 460 28V0H728V28C647 34 639 39 639 123V527C639 610 647 615 729 622V650Z" id="g190-73"></path><glyph.data ascent="989" descent="-360" horiz-adv-x="766" vert-adv-y="766"></glyph.data></g><g transform="matrix(.0095,0,0,-0.0095,25.655,3.264)"><path d="M462 177V227H365V632H320C217 496 116 350 21 208V177H284V109C284 43 280 38 190 31V0H451V31C369 38 365 43 365 108V177H462ZM284 227H88C155 336 218 430 282 519H284V227Z" id="g50-53"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="487" vert-adv-y="487"></glyph.data></g></svg>, Pd/C; c, CSC<svg height="12.9101pt" id="M14" style="vertical-align:-3.26379pt" version="1.1" viewbox="0 -9.64631 8.0591 12.9101" width="8.0591pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.0135,0,0,-0.0135,0,0)"><path d="M238 0V26C174 32 166 38 166 104V712C132 700 70 683 18 677V653C81 647 87 645 87 577V104C87 38 78 32 15 26V0H238Z" id="g190-109"></path><glyph.data ascent="989" descent="-360" horiz-adv-x="253" vert-adv-y="253"></glyph.data></g><g transform="matrix(.0095,0,0,-0.0095,3.441,3.264)"><path d="M414 144C384 79 371 75 317 75H135L276 221C367 316 408 376 408 465C408 570 327 635 237 635C179 635 131 609 100 575L42 494L67 471C94 510 138 565 205 565C277 565 321 517 321 435C321 348 258 270 195 195C146 137 88 81 33 26V0H411C423 44 433 88 446 135L414 144Z" id="g50-51"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="487" vert-adv-y="487"></glyph.data></g></svg>; d, reflux, pyridine; e, MeI; f, Raney Ni; g, <svg height="12.2733pt" id="M15" style="vertical-align:-3.26375pt" version="1.1" viewbox="0 -9.00955 30.3278 12.2733" width="30.3278pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.0135,0,0,-0.0135,0,0)"><path d="M729 650H468V622C546 615 554 610 554 527V365H213V527C213 610 221 616 297 622V650H38V622C120 616 128 611 128 527V123C128 39 120 34 40 28V0H303V28C221 34 213 40 213 123V322H554V123C554 39 546 34 460 28V0H728V28C647 34 639 39 639 123V527C639 610 647 615 729 622V650Z" id="g190-73"></path><glyph.data ascent="989" descent="-360" horiz-adv-x="766" vert-adv-y="766"></glyph.data></g><g transform="matrix(.0095,0,0,-0.0095,10.417,3.264)"><path d="M414 144C384 79 371 75 317 75H135L276 221C367 316 408 376 408 465C408 570 327 635 237 635C179 635 131 609 100 575L42 494L67 471C94 510 138 565 205 565C277 565 321 517 321 435C321 348 258 270 195 195C146 137 88 81 33 26V0H411C423 44 433 88 446 135L414 144Z" id="g50-51"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="487" vert-adv-y="487"></glyph.data></g><g transform="matrix(.0135,0,0,-0.0135,15.551,0)"><path d="M381 665C170 665 44 498 44 318C44 125 188 -15 369 -15C552 -15 703 117 703 333C703 534 550 665 381 665ZM359 629C491 629 601 517 601 306C601 114 502 21 390 21C249 21 146 158 146 346S248 629 359 629Z" id="g190-80"></path><glyph.data ascent="989" descent="-360" horiz-adv-x="747" vert-adv-y="747"></glyph.data></g><g transform="matrix(.0095,0,0,-0.0095,25.709,3.264)"><path d="M414 144C384 79 371 75 317 75H135L276 221C367 316 408 376 408 465C408 570 327 635 237 635C179 635 131 609 100 575L42 494L67 471C94 510 138 565 205 565C277 565 321 517 321 435C321 348 258 270 195 195C146 137 88 81 33 26V0H411C423 44 433 88 446 135L414 144Z" id="g50-51"></path><glyph.data ascent="3443" descent="-2856" horiz-adv-x="487" vert-adv-y="487"></glyph.data></g></svg>; h, ClCO<sub>2</sub>Et; i, heat at 200°C, 2 h; j, Ac<sub>2</sub>O; k, LiAlH<sub>4</sub>.</table>

Journal of Chemistry

sch22

Scheme 22

Scheme 22: Fused Imidazopyrazoles: Synthetic Strategies and Medicinal Applications 